Sodium hydride → HCID 21493029, compound

Reaction equation

[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.[H-].[Na+].[CH3:10][N:11]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]1S(C)(=O)=O>CN(C)C=O>[CH3:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[S:1][C:12]1[N:11]([CH3:10])[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=1

Participants

Procedure

A solution of 11.4 g of 2-mercapto-1-methyl-imidazole in 60 ml of dimethylformamide is added dropwise over the course of 15 minutes to a suspension of 4.8 g of 50% strength sodium hydride in 100 ml of dimethylformamide at 20° to 30° C, whilst stirring. The resulting solution is then added dropwise over the course of 30 minutes to a solution of 20.5 g of 1-methyl-2-methylsulphonyl-5-nitro-imidazole in 80 ml of dimethylformamide at 20° to 30° C whilst stirring. Thereafter the reaction mixture is stirred for a further hour at 100° C and is evaporated. The evaporation residue is extracted by shaking with 200 ml of methylene chloride and 200 ml of water and the methylene chloride extract is separated off, washed with 50 ml of water, dried over anhydrous magnesium sulphate and evaporated. After two recrystallisations from ethyl acetate the evaporation residue yields pure 1-methyl-2-[(1-methyl-5-nitro-2-imidazolyl)mercapto]-imidazole of melting point 123°-124° C.