DD201776A5 - Verfahren zur herstellung von 2-chloracet-essigsaeureamiden - Google Patents
Verfahren zur herstellung von 2-chloracet-essigsaeureamiden Download PDFInfo
- Publication number
- DD201776A5 DD201776A5 DD82238402A DD23840282A DD201776A5 DD 201776 A5 DD201776 A5 DD 201776A5 DD 82238402 A DD82238402 A DD 82238402A DD 23840282 A DD23840282 A DD 23840282A DD 201776 A5 DD201776 A5 DD 201776A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- substituted
- preparation
- diketene
- alkoxyaryl
- alkoxyalkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 6
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract description 4
- 229910021529 ammonia Inorganic materials 0.000 abstract description 3
- 150000003335 secondary amines Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LBHYOONLWAWEAA-UHFFFAOYSA-N 2-chloro-3-oxo-n-phenylbutanamide Chemical compound CC(=O)C(Cl)C(=O)NC1=CC=CC=C1 LBHYOONLWAWEAA-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- -1 methylethyl Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- AOOLFYMBFIGYDE-UHFFFAOYSA-N 2-chloro-3-oxobutanamide Chemical class CC(=O)C(Cl)C(N)=O AOOLFYMBFIGYDE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- VCBFAUSKNYAKJZ-UHFFFAOYSA-N 2-chloro-3-oxobutanoic acid Chemical compound CC(=O)C(Cl)C(O)=O VCBFAUSKNYAKJZ-UHFFFAOYSA-N 0.000 description 2
- WNVYZJSJUQUVSZ-UHFFFAOYSA-N 2-chloro-3-oxobutanoyl chloride Chemical compound CC(=O)C(Cl)C(Cl)=O WNVYZJSJUQUVSZ-UHFFFAOYSA-N 0.000 description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CIWCUHJTQHWNTR-UHFFFAOYSA-N 2-chloro-3-oxo-n-propan-2-ylbutanamide Chemical compound CC(C)NC(=O)C(Cl)C(C)=O CIWCUHJTQHWNTR-UHFFFAOYSA-N 0.000 description 1
- QJACRCAPQIYMIH-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)C(Cl)C(C)=O QJACRCAPQIYMIH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- SRAXAXHQMCQHSH-UHFFFAOYSA-N n-benzyl-2-chloroacetamide Chemical compound ClCC(=O)NCC1=CC=CC=C1 SRAXAXHQMCQHSH-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2044/81A CH649077A5 (en) | 1981-03-26 | 1981-03-26 | Process for the preparation of 2-chloroacetamides |
| CH600481 | 1981-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201776A5 true DD201776A5 (de) | 1983-08-10 |
Family
ID=25689367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82238402A DD201776A5 (de) | 1981-03-26 | 1982-03-24 | Verfahren zur herstellung von 2-chloracet-essigsaeureamiden |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4801750A (fr) |
| EP (1) | EP0061657B1 (fr) |
| CA (1) | CA1212960A (fr) |
| CS (1) | CS228541B2 (fr) |
| DD (1) | DD201776A5 (fr) |
| DE (1) | DE3260263D1 (fr) |
| HU (1) | HU191350B (fr) |
| IL (1) | IL65246A (fr) |
| IN (1) | IN155969B (fr) |
| MX (1) | MX156361A (fr) |
| PL (1) | PL130583B1 (fr) |
| SU (1) | SU1181538A3 (fr) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB782773A (en) * | 1955-07-12 | 1957-09-11 | Distillers Co Yeast Ltd | Chlorination process |
| DE1237553B (de) * | 1961-08-14 | 1967-03-30 | Shell Int Research | Verfahren zur Herstellung eines alpha-Chlor-acetessigsaeureamids |
| GB1096689A (en) * | 1963-12-19 | 1967-12-29 | Midvale Heppenstall Company | Method and apparatus for slow pouring and casting metals |
| US3449421A (en) * | 1964-01-20 | 1969-06-10 | Shell Oil Co | Chlorination process |
| US3393202A (en) * | 1965-04-26 | 1968-07-16 | Uniroyal Inc | 2, 3-dihydro-5-carboxamido-6-methyl-1, 4-oxathins and method of making same |
| US3249499A (en) * | 1965-04-26 | 1966-05-03 | Us Rubber Co | Control of plant diseases |
| CH492668A (de) * | 1968-07-04 | 1970-06-30 | Lonza Ag | Verfahren zur Herstellung von Acetessigsäuren |
| US3852351A (en) * | 1972-10-02 | 1974-12-03 | Fmc Corp | Chlorination of acetoacetamides |
| US4093654A (en) * | 1977-03-31 | 1978-06-06 | Hoffmann-La Roche Inc. | Production of pyridoxine intermediates from diketene |
| DE2824046A1 (de) * | 1978-06-01 | 1979-12-06 | Wacker Chemie Gmbh | Verfahren zur herstellung von alpha- chloracetoacetamiden |
| US4214002A (en) * | 1978-08-17 | 1980-07-22 | Givaudan Corporation | Preservation of aqueous systems with 2-chloro-3-oxobutyramide derivatives |
| IN151753B (fr) * | 1980-04-02 | 1983-07-23 | Lonza Ag |
-
1982
- 1982-03-15 IL IL65246A patent/IL65246A/xx unknown
- 1982-03-17 EP EP82102187A patent/EP0061657B1/fr not_active Expired
- 1982-03-17 DE DE8282102187T patent/DE3260263D1/de not_active Expired
- 1982-03-19 IN IN307/CAL/82A patent/IN155969B/en unknown
- 1982-03-23 PL PL1982235580A patent/PL130583B1/pl unknown
- 1982-03-24 DD DD82238402A patent/DD201776A5/de unknown
- 1982-03-24 US US06/361,333 patent/US4801750A/en not_active Expired - Fee Related
- 1982-03-24 CS CS822054A patent/CS228541B2/cs unknown
- 1982-03-25 HU HU82908A patent/HU191350B/hu not_active IP Right Cessation
- 1982-03-25 MX MX191974A patent/MX156361A/es unknown
- 1982-03-25 SU SU823449351A patent/SU1181538A3/ru active
- 1982-03-26 CA CA000399488A patent/CA1212960A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PL130583B1 (en) | 1984-08-31 |
| DE3260263D1 (en) | 1984-07-26 |
| HU191350B (en) | 1987-02-27 |
| CA1212960A (fr) | 1986-10-21 |
| PL235580A1 (fr) | 1982-11-08 |
| CS228541B2 (en) | 1984-05-14 |
| IL65246A0 (en) | 1982-05-31 |
| SU1181538A3 (ru) | 1985-09-23 |
| EP0061657A1 (fr) | 1982-10-06 |
| IN155969B (fr) | 1985-04-20 |
| EP0061657B1 (fr) | 1984-06-20 |
| IL65246A (en) | 1985-11-29 |
| US4801750A (en) | 1989-01-31 |
| MX156361A (es) | 1988-08-12 |
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