2-Mercapto-1 -methyl-imidazole

Mercapto-methyl-imidazole Allylbromide Cationic effect... 

Aus 2-Mercapto-imidazol wird mit Formaldehyd/Dimethylamin in Essigsaure bei 4" 1-Hydro-xymethyl-2-mercapto-imidazol gebildet (71 %)732. Dagegen wird aus 2-Mercapto-4(5)-methyl-imidazol unter den selben Reaktionsbedingungen 4(5)-Hydroxymethyl-2-mercapto-5(4)-me-thyl-imidazol (82%) crhalten732. 

Aus 2-Mercapto-4(5)-methyl-imidazol kann durch direkte Formylierung mit Trichlormethan und Kaliumhydroxid in Ethanol/Wasser 4(5) -Formyl-2-mercapto-5 (4) -methyl-imidazol herge-stellt werden (s. Bd. VII/1, S. 38). 

Methimazole, 2-mercapto-l-methyl-imidazole, useful in thyrotoxicosis, is usually given as the 2-ethoxycarbonyl-derivative (3.44) (carbimazole, Neo-Mercazole ) which forms a depot. 

Imidazole, 1 -hydroxy-2,4,5-triphenyl-3-oxides reactions, S, 455 Imidazole, iodo-nitrodehalogenation, 5, 396-397 Imidazole, 1-iodo-reactions, S, 454 stability, S, 110 Imidazole, 2-iodo-synthesis, S, 401 Imidazole, N-iodo-, S, 393 reactions, 5, 454 Imidazole, 4-iodo-5-methyl-iodination, 5, 400 Imidazole, 2-isopropyl-4-nitro-N-nitration, 5, 351 Imidazole, 2-lithio-reactions, S, 106, 448 Imidazole, 2-mercapto-l-methyl-as antithyroid drug, 1, 171 mass spectra, 5, 358 Imidazole, 1-methoxymethyl-acylation, S, 402 Imidazole, 5-methoxy-l-methyl-reactions... 

The l-acyl-3-methylimidazole-2-thiones are easily obtained either from bis-l-methyl-2-imidazole disulfide, a carboxylic acid, and triphenylphosphine, or from 2-mercapto-l-methylimidazole and a carboxylic acid chloride in the presence of triethylamine.[32 ... 

Ochiai, who reported in 1936 the first synthesis of the imidazo[2,l-h]thia-zole system (36CB1650), transformed ethyl 2-mercapto-5-methyl-imidaz-oIe-4-carboxylate with monochloroacetone into 2-(acylalkylthio)-imidazole 36. Refluxing 36 in phosphorus oxychloride yields ethyl 3,5-dimethylim-idazo[2,l-h]thiazole-6-carboxylate. No cyclization could be achieved by heating 36 in acetic anhydride because N-acylation (to 37) inhibited further reaction to the bicyclic system. 

Substituierte l-(Ethoxycarbonyl-methyl)-4-mercapto-5-phenyl-imidazole allgemeine Arbeitsvorschrift78 ... 

Einen einfachen Zugang zu 4(5)-(Mercapto-thiocarbonyl)-imidazolen ermoglicht die Umsetzung von Natrium-imidazoliden in Dimethylsulfoxid oder der freien Imidazole mit Na-triumhydroxid in Pyridin oder Methyl-pyridinen mit Schwefelkohlenstoff699. Fiir Imidazol selbst wurde nur eine Ausbeute von 2% beschrieben. Mit 2-substituierten bzw. 2,4(5)-disub-stituierten Imidazolen liegen die Ausbeuten dagegen zwischen 60 und 90%. 

Brom-5-formyl-l-( 4-methoxy-henzyl)-imidazol l-Benzyl-4-brom-5-carboxy-...946 /-Benzyl-4-brom-5-mercapto-...946 4-Brom-5-methoxycarbonyl-]-methyl-...1047 1033 50% 67% 68% 50% ... 

Thione groups can often be eliminated by oxidation probably the sulfinic acid is the intermediate. Sometimes the sulfinic acid can be isolated (e.g., 740 741), but more often it spontaneously loses SO2. In this way, thiazoline-2-thiones give thiazoles, l,2-dithiole-3-thiones 742 are converted into 1,2-dithiolylium salts 743, l,3-dithiole-2-thiones 744 into 1,3-dithiolylium salts 745, 1,5-disubstituted imidazole-2-thiones into imidazoles <2003JHC229>, and 3-mercapto-l,2,4-triazoles into the parent triazole <2006S156>. In the pyrazole series, 746 also loses an A-methyl group to yield 747. 

Imidazol 5-(Ethylthio-methyl)-4-hydroxy-2-mercapto- E8c, 45 [RS - CH2 - CH(NH2) - COOH + NHtS-CN]... 

Imidazol 4,5-Dimethoxycarbonyl-2-mercapto-1 -methyl- E8c, 43 [OHC-N(CH3)-CH2-COOR/ROOC - COOR/RONa + KS-CN]... 

Imidazol 2-Mercapto-1-phenyl-tetrahydro- IV/Id, 252 IsothioharnstofT N-Benzyl-S-methyl-E4, 604 (aus dem Salz)... 

METHYLNITROIMIDAZOLYLMERCAPTOPURINE 6-(T-METHYL-4 -NITRO-5 -IMIDAZOLYL)-MERCAPTO-PURINE 6-(METHYL-p-NITRO-5-IMIDAZOLYL)-THIOPURINE 6-(l-METHYL-p-NITRO-5-IMIDAZOL-YL)-THIOPURINE 6-((l-METHYL-4-NITROIMIDAZOL-5-YL)THIO)PURINE 6-(l-METHYL-4-NITROIMIDAZ-OL-5-YLTHIO)PURINE 6-((l-METHYL-4-NITRO-lH-IMDAZOL-5-YL)THIO)-lH-PURINE NCI-C03474 NSC-39084 RORASUL... 

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