NO810928L - Fremgangsmaate ved fremstilling av n-methylenether-substituerte 2-halogenacetamider - Google Patents
Fremgangsmaate ved fremstilling av n-methylenether-substituerte 2-halogenacetamiderInfo
- Publication number
- NO810928L NO810928L NO810928A NO810928A NO810928L NO 810928 L NO810928 L NO 810928L NO 810928 A NO810928 A NO 810928A NO 810928 A NO810928 A NO 810928A NO 810928 L NO810928 L NO 810928L
- Authority
- NO
- Norway
- Prior art keywords
- chloroacetanilide
- methyl
- reacted
- radical
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 cycloalkenyl radical Chemical group 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 16
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002808 molecular sieve Substances 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- KJRMSQTZYYYYAI-UHFFFAOYSA-N 2-chloro-N-(methoxymethyl)-N-phenylbutanamide Chemical compound C(C)C(C(=O)N(C1=CC=CC=C1)COC)Cl KJRMSQTZYYYYAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- MSWKVHMWEIWAEL-UHFFFAOYSA-N 2-chloro-2-ethyl-n-(methoxymethyl)-n-phenylbutanamide Chemical compound CCC(Cl)(CC)C(=O)N(COC)C1=CC=CC=C1 MSWKVHMWEIWAEL-UHFFFAOYSA-N 0.000 claims 1
- ANGFDWGRJQAHNC-UHFFFAOYSA-N 2-chloro-N-(ethoxymethyl)-N-phenylbutanamide Chemical compound C(C)C(C(=O)N(C1=CC=CC=C1)COCC)Cl ANGFDWGRJQAHNC-UHFFFAOYSA-N 0.000 claims 1
- BKSYVPGPNXHYFP-UHFFFAOYSA-N 2-chloro-N-(ethoxymethyl)-N-phenylpropanamide Chemical compound CC(C(=O)N(C1=CC=CC=C1)COCC)Cl BKSYVPGPNXHYFP-UHFFFAOYSA-N 0.000 claims 1
- VJULAACBOCJUCR-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-ethyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(CC)C=CC=C1C(F)(F)F VJULAACBOCJUCR-UHFFFAOYSA-N 0.000 claims 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- UUWBBAQAKKYQKN-UHFFFAOYSA-N n-(butoxymethyl)-2-chloro-2-ethyl-n-phenylbutanamide Chemical compound CCCCOCN(C(=O)C(Cl)(CC)CC)C1=CC=CC=C1 UUWBBAQAKKYQKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MGSXWVBFRJCQMZ-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(methoxymethyl)acetamide Chemical compound COCN(C(=O)CCl)C1=C(C)CCCC1C MGSXWVBFRJCQMZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005690 transetherification reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ACXVSJIQMCVKCA-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(2-methylpropoxymethyl)acetamide Chemical compound CC(C)COCN(C(=O)CCl)C1=C(C)CCCC1C ACXVSJIQMCVKCA-UHFFFAOYSA-N 0.000 description 1
- NELAASWIGOQAPS-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(prop-2-ynoxymethyl)acetamide Chemical compound CC1CCCC(C)=C1N(COCC#C)C(=O)CCl NELAASWIGOQAPS-UHFFFAOYSA-N 0.000 description 1
- TXEDFACFWKJZGO-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=C(C)CCCC1C TXEDFACFWKJZGO-UHFFFAOYSA-N 0.000 description 1
- QHOLUFMPUPBPNN-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-[(2-methylpropan-2-yl)oxymethyl]acetamide Chemical compound CC1CCCC(C)=C1N(COC(C)(C)C)C(=O)CCl QHOLUFMPUPBPNN-UHFFFAOYSA-N 0.000 description 1
- IYLMCARCSCXVNP-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=C(C)C=CC=C1C IYLMCARCSCXVNP-UHFFFAOYSA-N 0.000 description 1
- YGTYRMDZBFYUCE-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound COC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl YGTYRMDZBFYUCE-UHFFFAOYSA-N 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- 229910017090 AlO 2 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000003931 anilides Chemical group 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/133,752 US4296254A (en) | 1980-03-25 | 1980-03-25 | Transetherification in amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810928L true NO810928L (no) | 1981-09-28 |
Family
ID=22460147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810928A NO810928L (no) | 1980-03-25 | 1981-03-18 | Fremgangsmaate ved fremstilling av n-methylenether-substituerte 2-halogenacetamider |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4296254A (fr) |
| JP (1) | JPS56145259A (fr) |
| KR (1) | KR840000417B1 (fr) |
| AT (1) | AT371103B (fr) |
| AU (1) | AU6848281A (fr) |
| BE (1) | BE887999A (fr) |
| BR (1) | BR8101605A (fr) |
| CA (1) | CA1167458A (fr) |
| DD (1) | DD157335A5 (fr) |
| DE (1) | DE3110420A1 (fr) |
| DK (1) | DK120781A (fr) |
| ES (1) | ES500468A0 (fr) |
| FR (1) | FR2479195A1 (fr) |
| GB (1) | GB2072182B (fr) |
| IL (1) | IL62410A0 (fr) |
| IT (1) | IT1144663B (fr) |
| LU (1) | LU83231A1 (fr) |
| NL (1) | NL8101324A (fr) |
| NO (1) | NO810928L (fr) |
| NZ (1) | NZ196542A (fr) |
| PH (1) | PH16404A (fr) |
| PL (1) | PL129316B1 (fr) |
| PT (1) | PT72677B (fr) |
| RO (1) | RO81694A (fr) |
| SE (1) | SE8101728L (fr) |
| YU (1) | YU71081A (fr) |
| ZA (1) | ZA811800B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4798618A (en) * | 1981-12-10 | 1989-01-17 | Agro-Kanesho Co., Ltd. | Novel chloroacetanilide derivatives and herbicides containing the same for use in paddy field |
| WO2005090299A2 (fr) * | 2004-03-12 | 2005-09-29 | Wyeth | Carbamates utilises en tant qu'agents anti-vih |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2617747A (en) * | 1950-06-28 | 1952-11-11 | Merck & Co Inc | Mothproofing |
| US2914553A (en) * | 1955-09-22 | 1959-11-24 | Distillers Co Yeast Ltd | Alcoholysis of aromatic carboxylic acid amides with polyhydric alcohols |
| US3692691A (en) * | 1971-05-17 | 1972-09-19 | Ethyl Corp | Preparation of dihydrocarbyl 2- or 4-hydroxybenzyl c4-20 alkyl ethers |
| US4156784A (en) * | 1974-12-18 | 1979-05-29 | Basf Aktiengesellschaft | Manufacture of carbamates |
-
1980
- 1980-03-25 US US06/133,752 patent/US4296254A/en not_active Expired - Lifetime
-
1981
- 1981-03-18 FR FR8105438A patent/FR2479195A1/fr active Pending
- 1981-03-18 RO RO81103730A patent/RO81694A/fr unknown
- 1981-03-18 CA CA000373279A patent/CA1167458A/fr not_active Expired
- 1981-03-18 PH PH25373A patent/PH16404A/en unknown
- 1981-03-18 IL IL62410A patent/IL62410A0/xx unknown
- 1981-03-18 PT PT72677A patent/PT72677B/pt unknown
- 1981-03-18 DE DE19813110420 patent/DE3110420A1/de not_active Ceased
- 1981-03-18 YU YU00710/81A patent/YU71081A/xx unknown
- 1981-03-18 NL NL8101324A patent/NL8101324A/nl not_active Application Discontinuation
- 1981-03-18 BR BR8101605A patent/BR8101605A/pt unknown
- 1981-03-18 JP JP3808281A patent/JPS56145259A/ja active Pending
- 1981-03-18 GB GB8108384A patent/GB2072182B/en not_active Expired
- 1981-03-18 DK DK120781A patent/DK120781A/da not_active Application Discontinuation
- 1981-03-18 ZA ZA00811800A patent/ZA811800B/xx unknown
- 1981-03-18 NO NO810928A patent/NO810928L/no unknown
- 1981-03-18 PL PL1981230208A patent/PL129316B1/pl unknown
- 1981-03-18 BE BE0/204166A patent/BE887999A/fr not_active IP Right Cessation
- 1981-03-18 IT IT20415/81A patent/IT1144663B/it active
- 1981-03-18 AU AU68482/81A patent/AU6848281A/en not_active Abandoned
- 1981-03-18 NZ NZ196542A patent/NZ196542A/xx unknown
- 1981-03-18 KR KR1019810000879A patent/KR840000417B1/ko not_active Expired
- 1981-03-18 LU LU83231A patent/LU83231A1/fr unknown
- 1981-03-18 SE SE8101728A patent/SE8101728L/xx not_active Application Discontinuation
- 1981-03-18 ES ES500468A patent/ES500468A0/es active Granted
- 1981-03-18 DD DD81228411A patent/DD157335A5/de unknown
- 1981-03-18 AT AT0126581A patent/AT371103B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RO81694B (ro) | 1983-05-30 |
| DK120781A (da) | 1981-09-26 |
| GB2072182A (en) | 1981-09-30 |
| AU6848281A (en) | 1981-10-01 |
| AT371103B (de) | 1983-06-10 |
| ES8207509A1 (es) | 1982-09-16 |
| NL8101324A (nl) | 1981-10-16 |
| CA1167458A (fr) | 1984-05-15 |
| DD157335A5 (de) | 1982-11-03 |
| FR2479195A1 (fr) | 1981-10-02 |
| DE3110420A1 (de) | 1981-12-24 |
| NZ196542A (en) | 1983-03-15 |
| PH16404A (en) | 1983-09-26 |
| PL129316B1 (en) | 1984-04-30 |
| KR830005111A (ko) | 1983-07-23 |
| IL62410A0 (en) | 1981-05-20 |
| YU71081A (en) | 1983-10-31 |
| RO81694A (fr) | 1983-06-01 |
| JPS56145259A (en) | 1981-11-11 |
| US4296254A (en) | 1981-10-20 |
| IT1144663B (it) | 1986-10-29 |
| KR840000417B1 (ko) | 1984-04-02 |
| LU83231A1 (fr) | 1981-10-30 |
| PT72677A (en) | 1981-04-01 |
| ZA811800B (en) | 1982-05-26 |
| BE887999A (fr) | 1981-09-18 |
| ATA126581A (de) | 1982-10-15 |
| BR8101605A (pt) | 1981-09-29 |
| ES500468A0 (es) | 1982-09-16 |
| GB2072182B (en) | 1984-02-29 |
| IT8120415A0 (it) | 1981-03-18 |
| PL230208A1 (fr) | 1981-11-13 |
| PT72677B (en) | 1982-03-22 |
| SE8101728L (sv) | 1981-11-09 |
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