US2519310A - Preparation of 2-mercaptoimidazole - Google Patents
Preparation of 2-mercaptoimidazole Download PDFInfo
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- US2519310A US2519310A US62980A US6298048A US2519310A US 2519310 A US2519310 A US 2519310A US 62980 A US62980 A US 62980A US 6298048 A US6298048 A US 6298048A US 2519310 A US2519310 A US 2519310A
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- US
- United States
- Prior art keywords
- mercaptoimidazole
- sodium
- added
- solution
- ammonia
- Prior art date
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- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VHXGNEJJQGMRGL-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione;sodium Chemical compound [Na].S=C1NC=CN1 VHXGNEJJQGMRGL-UHFFFAOYSA-N 0.000 description 2
- LKIVEIAXFZBGMO-UHFFFAOYSA-N 1-methyl-2-methylsulfanylimidazole Chemical compound CSC1=NC=CN1C LKIVEIAXFZBGMO-UHFFFAOYSA-N 0.000 description 2
- MIPOOVYZQKVTLI-UHFFFAOYSA-N 4-propyl-1,3-dihydroimidazole-2-thione Chemical compound CCCC1=CNC(=S)N1 MIPOOVYZQKVTLI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal amide Chemical class 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NPBMCLWRSOFTTI-UHFFFAOYSA-N 2-benzylsulfanyl-1h-imidazole Chemical compound C=1C=CC=CC=1CSC1=NC=CN1 NPBMCLWRSOFTTI-UHFFFAOYSA-N 0.000 description 1
- ZZKKGEQXOTVRRU-UHFFFAOYSA-N 2-ethylsulfanyl-1h-imidazole Chemical compound CCSC1=NC=CN1 ZZKKGEQXOTVRRU-UHFFFAOYSA-N 0.000 description 1
- AHRKNMZGVFUHOT-UHFFFAOYSA-N 3-methyl-1h-imidazole-2-thione;sodium Chemical compound [Na].CN1C=CNC1=S AHRKNMZGVFUHOT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003200 antithyroid agent Substances 0.000 description 1
- 229940043671 antithyroid preparations Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- MZWKCFGWAWRHDY-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] 2,2-diphenylethanethioate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 MZWKCFGWAWRHDY-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/84—Sulfur atoms
Definitions
- the new. process of the. present -invention involves the cleavage of ai thioether with l an alkali metalas -illustrated by the. followingffm equation:
- R an" alkyl' or' aralkyl radical. 1i resuIting' prdduct, anialkali nietal saltfbf the fi Ii mercaritoimidazole; -is readily converted to the The ' de'sired free "-mercaptoimidazol' by neutralization with an acid or by treatment-*vvitha'salt diverse agents" as P235, dry hydrogem chloride,
- reaction be conducted in liquid ammonia which serves as a solvent and tends to reduce the hazards of the reaction.
- Example 3 To g. (0.026 mole) of 2-benzylthioimidazole dissolved in liquid ammonia were added 1.79 g. (0.078 mole) of sodium. The blue solution was stirred for about one hour and then water was added. The ammonia and water were removed using reduced pressure, and the residue was neutralized with dilute HCl. Recrystallization of 2.8 g. of crude material from water gave 1 g. (38% yield) of pure Z-mercaptoimidazole,
- Example 4 Two grams of 2-methylthio-4(5)-n propylimidazole was dissolved in liquid ammonia and .88 g. (0.0384 gram atom) sodium was added. After stirring for one hour, some blue color remained. About 5 cc. of alcohol were added and then the excess ammonia and the alcohol were removed. To the residue was added about cc. of water and then the solution was neutralized with HCl. Two grams of crude material separated. This was recrystallized once from Water using activated charcoal. One gram of 4(5) n-propyl-Z-mercaptoimidazole melting at 182-183 C. was obtained, filtered and dried.
- Example 5 Five grams of 1-methyl-2-mercaptoimidazole was dissolved as much as possible in chloroform and grams of methyl iodide was added. The solution was refluxed for two hours and then cooled. A small amount of solid was filtered. The solution was concentrated and the residue treated with ether. Five grams of solid were obtained, melting at around 145 C. The hydroiodide salt of the desired compound is reported to melt at 148 C. (Marckwald, Ber. 22, 1356). The solid was dissolved in water and treated with potassium carbonate. It was finally found that the free base was not obtained in any quantity until the pH was brought up to 11 with potassium hydroxide solution. At this pH a sharp mercaptan-like odor was noticed. The solution was concentrated and the residue was treated with ether. The ether solution was dried briefly over potassium hydroxide and then was concentrated. This oily residue was dried in a desiccator. One gram 0.
- the process of preparing alkali metal salts of Z-mercaptoimidazoles which comprises the step of treating a 2-mercaptoimidazolethioether having the general formula of treating a 2-mercaptoimidazolethioether having the general formula in which R is a radical of the group consisting of hydrogen and alkyl radicals and R is a member of the group consisting of alkyl and aralkyl radicals, with metallic sodium in liquid ammonia whereby the thioether is cleaved and a sodium Z-mercaptoimidazole is obtained.
- a method of preparing sodium Z-mercaptoimidazole which comprises treating a 2-alkylmercaptoimidazole with sodium in liquid ammonia whereby sodium 2-mercaptoimidazole is formed.
- a method of preparing sodium 2-mercaptoimidazole which comprises treating Z-methylmercaptoimidazole with sodium in liquid ammonia whereby sodium Z-mercaptoimidazole is formed.
- a method of preparing sodium 4(5)-n propyl-2-mercaptoimidazole which comprises treating 2-methylthio-4(5)-n propylimidazole with sodium in liquid ammonia whereby sodium 4(5) n propyl-2-mercaptoimidazole is formed.
- a method of preparing sodium l-methyl- Z-mercaptoimidazole which comprises treating 1-methyl-2-methylthioimidazole with sodium in liquid ammonia whereby sodium 1-methyl-2- mercaptoimidazole is formed.
- R I3 I3 R N N-R in in which R is a member of the group consisting of hydrogen and alkyl radicals and R is a memher of the group consisting of alkyl and aralkyl radicals with an alkali metal in liquid ammonia and after reaction thereof whereby the thioether linkage is cleaved, neutralizing the reaction product with an acid to obtain 2-mercaptoimidazoles having the first illustrated formula above.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
though tests 'made r also active as anti thyroid agents.
Patented Aug. 15, 1950 2,519,310 l PREPARAT IUN-OF Z-MERGAPT'O IM ID AZOLE :Alic M. Dessert-,' Old Greenwich, Conmg'as'signor to -An'ieri'cari CyanamidxCompanw New York, n'N':-'Y.'; a corporation of Maine "No'DraWing, Application December 1, 1948, "Serial No. 62,980
'2 Claims.
-ing.-.alkyl substituents vin ithe. imidaaole .ring are T It appears -likely, .therefore, .thatthere will be. a demand for considerable quantities of these. compounds .foruse in medicine.
-- mercaptoimidazoles are obtained. 1 the potential l l demand for 1 large quantities of flUnfortunately presently J.known methods. of, preparing thel' 2-mercapto-' imid'azoles are not satisfactory.
' Marckwald described the s'production of l '2- mercaptoimidazole as early as 1892 in" Berichte,
volume 25, page 2354. *He'used as starting materials aminoacetal'-' and potassium thiocyanate in an involved process requiring many steps. The product of the reaction is difficult to handle,
and extremely low *yields of the desired 2- 2-rnercaptoimidazole l and alkyl rnercaptoimid- 'azoles -it isdesirable; thereiore, that a method 1 of rproducing these substances on a commercial scale be made available. Ihe present invention describes such-a. method, which uses readily 30 available materialsand .g1ves, under-fav0rable -conditions; almost quantitative yields.
. In brief the new. process of the. present -invention involves the cleavage of ai thioether with l an alkali metalas -illustrated by the. followingffm equation:
-.radicaland: R: an" alkyl' or' aralkyl radical. 1i resuIting' prdduct, anialkali nietal saltfbf the fi Ii mercaritoimidazole; -is readily converted to the The ' de'sired free "-mercaptoimidazol' by neutralization with an acid or by treatment-*vvitha'salt diverse agents" as P235, dry hydrogem chloride,
"sodium metal in ethah'oL" acetic acid," and-hydrogen iodide? and still other agentswhich" have "been usedebefore to cleave thioethers wereun- 5 able tocleavlth 2-mereaptoimidazolethioethers --whiclr are usedherein as intermediates.
It is preferred that the reaction be conducted in liquid ammonia which serves as a solvent and tends to reduce the hazards of the reaction.
\ The "temperature of the reaction is not"'ci-itical,
-'"but care'should be" taken to keep thereaction mixture-in liquid 'form'to reduce the" d'ahg'eriof an explosion ifrom the sod-amide; which maybe formed under these 'c'Ohditi'bnsfiby the addition,
Ordinarilyy "der'these'conditions the reactiontakes placc at low "temperatures," but in" pressure vessels it possible to keep 'the"'ammonia' in liquid form at higher temperatures. Sodium is the preferred alkali metal because of its cheapness, -but other alkali-"metals' 'slichas potassiumor if lithium mayhe used. Theoretically," the" "reaction requires"at least two mhles'of the alkali metal for*"each"1n'ole- 0f"=the f mercaptoimidazoleti iio tl'ierfbutit"is preferld th'at three 170 seven mores-or the 'allialinfetal be used. c
The reaction takes place "within a" very short time" and "is-generally" considered to becO'mp'1ete *whenthe blue" color "of *the" alkali metal in" the -li'quid arhmenia'-disappears. W'ater is then added -'to"- decompose the alkali metal amide," and "the ammonia and-waterremoved by evaporation. The product contains*the alkali-metalsaltbf the Z-mercaptoimidazole. 7 On neutralization with an acid or ammonium chloride or the like the fre m'ercaptoimidaaole"is obtained mcxcel- 1 1 nt yie1ds. Thec'rude '-'product may be pari- -fied by recrystallization from solvents.
Examples showing 3 the preparation of '2- 2 40 "mercaptoi'mldazole and alkylsubstituted mercaptoimidazoles from representative Z-tlkyl and 2 arallylthioimidazoles"willnow beEiven. *It "#Will be"understood; of --coursethat' other 2 a1ky1 ana z-aralkylthicimidazcles may be used and at the process is=not limi-ted to -the "exactconditions described.
lExamplc l To" 1 1 :40: g, 0.94 resale) of rlfethyl 'iso'thi'ourea e distill-ed.ibromacetaldehyde; and th' mirture was stirredron t /z hou rs on a steam bath at' 85?7C. The; solution was made basic with r otassium carbonate s sblution and tifen th'er 'ei-tracted. For example; such;jfb5-.. Concerrtrationcof the' ethcr asolution," gave 2- Mixed melting point by another process was Example 2 To a solution of 4.4 g. (0.034 mole) of 2-ethylthioimidazole in liquid ammonia were added 2.5 g. (0.102 mole) of sodium. In 40 minutes the blue color disappeared, and water was added to the solution. The ammonia and water were removed at low pressure, and the residue was neutralized with dilute HCl. An acetone extraction of the solid obtained gave 3.3 g. 97% yield) of Z-mercaptoimidazole melting at about 226 0.
Example 3 To g. (0.026 mole) of 2-benzylthioimidazole dissolved in liquid ammonia were added 1.79 g. (0.078 mole) of sodium. The blue solution was stirred for about one hour and then water was added. The ammonia and water were removed using reduced pressure, and the residue was neutralized with dilute HCl. Recrystallization of 2.8 g. of crude material from water gave 1 g. (38% yield) of pure Z-mercaptoimidazole,
Example 4 Two grams of 2-methylthio-4(5)-n propylimidazole was dissolved in liquid ammonia and .88 g. (0.0384 gram atom) sodium was added. After stirring for one hour, some blue color remained. About 5 cc. of alcohol were added and then the excess ammonia and the alcohol were removed. To the residue was added about cc. of water and then the solution was neutralized with HCl. Two grams of crude material separated. This was recrystallized once from Water using activated charcoal. One gram of 4(5) n-propyl-Z-mercaptoimidazole melting at 182-183 C. was obtained, filtered and dried.
Example 5 Five grams of 1-methyl-2-mercaptoimidazole was dissolved as much as possible in chloroform and grams of methyl iodide was added. The solution was refluxed for two hours and then cooled. A small amount of solid was filtered. The solution was concentrated and the residue treated with ether. Five grams of solid were obtained, melting at around 145 C. The hydroiodide salt of the desired compound is reported to melt at 148 C. (Marckwald, Ber. 22, 1356). The solid was dissolved in water and treated with potassium carbonate. It was finally found that the free base was not obtained in any quantity until the pH was brought up to 11 with potassium hydroxide solution. At this pH a sharp mercaptan-like odor was noticed. The solution was concentrated and the residue was treated with ether. The ether solution was dried briefly over potassium hydroxide and then was concentrated. This oily residue was dried in a desiccator. One gram 0.
1-methyl-2-methylthioimidazole, possibly still wet, was obtained.
The gram of oily material obtained above was dissolved in liquid ammonia and 0.53 g. (0.0231 gram atom) of sodium was added. After onehalf hour the blue color had disappeared, and 5 cc. of alcohol were added. Then the excess ammonia and alcohol were removed. To the residue were added 10 cc. of water. This solution was neutralized with hydrochloric acid and then concentrated to dryness. The residue was treated with alcohol, filtered and the alcohol concentrated. The product, l-methyl-Z-mercaptoimidazole was recrystallized from water.
This is a continuation-in-part of my application, Serial No. 5,200, filed January 29, 1948, now abandoned.
I claim:
1. The process of preparing alkali metal salts of Z-mercaptoimidazoles which comprises the step of treating a 2-mercaptoimidazolethioether having the general formula of treating a 2-mercaptoimidazolethioether having the general formula in which R is a radical of the group consisting of hydrogen and alkyl radicals and R is a member of the group consisting of alkyl and aralkyl radicals, with metallic sodium in liquid ammonia whereby the thioether is cleaved and a sodium Z-mercaptoimidazole is obtained.
3. A method of preparing sodium Z-mercaptoimidazole which comprises treating a 2-alkylmercaptoimidazole with sodium in liquid ammonia whereby sodium 2-mercaptoimidazole is formed.
4. A method of preparing sodium 2-mercaptoimidazole which comprises treating Z-methylmercaptoimidazole with sodium in liquid ammonia whereby sodium Z-mercaptoimidazole is formed.
5. A method of preparing sodium 4(5)-n propyl-2-mercaptoimidazole which comprises treating 2-methylthio-4(5)-n propylimidazole with sodium in liquid ammonia whereby sodium 4(5) n propyl-2-mercaptoimidazole is formed.
6. A method of preparing sodium l-methyl- Z-mercaptoimidazole which comprises treating 1-methyl-2-methylthioimidazole with sodium in liquid ammonia whereby sodium 1-methyl-2- mercaptoimidazole is formed.
7. A method of preparing 2-mercaptoimidazoles having the general formula which comnrises treating a compound having the formula.
R I3: I3 R N N-R in in which R is a member of the group consisting of hydrogen and alkyl radicals and R is a memher of the group consisting of alkyl and aralkyl radicals with an alkali metal in liquid ammonia and after reaction thereof whereby the thioether linkage is cleaved, neutralizing the reaction product with an acid to obtain 2-mercaptoimidazoles having the first illustrated formula above.
ALICE M. DESSERT.
No references cited.
Claims (1)
- 7. A METHOD OF PREPARING 2-MERCAPTIOMIDAZOLES HAVING THE GENERAL FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62980A US2519310A (en) | 1948-12-01 | 1948-12-01 | Preparation of 2-mercaptoimidazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62980A US2519310A (en) | 1948-12-01 | 1948-12-01 | Preparation of 2-mercaptoimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2519310A true US2519310A (en) | 1950-08-15 |
Family
ID=22046109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US62980A Expired - Lifetime US2519310A (en) | 1948-12-01 | 1948-12-01 | Preparation of 2-mercaptoimidazole |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2519310A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671088A (en) * | 1951-04-02 | 1954-03-02 | Nat Res Dev | Antithyroid compounds |
| US3219522A (en) * | 1957-12-26 | 1965-11-23 | Pfizer & Co C | Process for controlling fungi with imidazoles, imidazolines, pyrimidines, and diazacyclooctenes and diazepines |
| US4182624A (en) * | 1977-07-19 | 1980-01-08 | Hoechst Aktiengesellschaft | Imidazole carboxylic acids and derivatives thereof |
-
1948
- 1948-12-01 US US62980A patent/US2519310A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671088A (en) * | 1951-04-02 | 1954-03-02 | Nat Res Dev | Antithyroid compounds |
| US3219522A (en) * | 1957-12-26 | 1965-11-23 | Pfizer & Co C | Process for controlling fungi with imidazoles, imidazolines, pyrimidines, and diazacyclooctenes and diazepines |
| US4182624A (en) * | 1977-07-19 | 1980-01-08 | Hoechst Aktiengesellschaft | Imidazole carboxylic acids and derivatives thereof |
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