C[N:2]1[C:6]([C:7](OCC)=[O:8])=[C:5]([C:12](OCC)=[O:13])[N:4]=[C:3]1[S:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.O.ClCCl>[CH3:18][S:17][C:3]1[NH:4][C:5]([CH2:12][OH:13])=[C:6]([CH2:7][OH:8])[N:2]=1
A solution of the above diethyl 2- (methylthio)-4,5-imidazoledicarboxylate (23 mmol) in freshly distilled anhydrous dichloromethane (50 mL) is added slowly to a stirred suspension of lithium aluminum hydride (69 mmol) in anhydrous ether (140 mL) at 0°-5° C. The mixture is stirred at about 0°-5° C. for about 3 hours after the addition is completed, then for about 1 hour at room temperature. The excess hydride is carefully decomposed by the slow, sequential addition of water (2.6 mL), 15% sodium hydroxide solution (2.6 mL), and water (7.8 mL). The precipitate of inorganic salts is filtered and extracted continuously for about 24 hours with tetrahydrofuran heated under reflux in a Soxhlet apparatus. The tetrahydrofuran solution is combined with the filtrate from the reaction mixture and concentrated to dryness in vacuo. The product is dried in vacuo and crystallized from tetrahydrofuran to give 2-(methylthio)-4,5-bis(hydroxymethyl) imidazole.
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