Sodium Hydroxide → HCID 23172629, compound

Participants

Reaction Steps

A solution of the above-identified diethyl 1-n-propyl-2-(methylthio)imidazole-4,5-dicarboxylate (23 mmol) in anhydrous dichloromethane (50 mL) was slowly (1 hour) added to a stirred suspension of lithium aluminum hydride (69 mmol) in anhydrous ether (140 mL) at 0.5° C. under nitrogen. The mixture was stirred at 0°-5° C. for 3 hours after the addition was completed, then at ambient temperature for 1 hour. The excess hydride was 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 was filtered and extracted continuously for 24 hours with tetrahydrofuran heated under reflux in a Soxhlet apparatus. The tetrahydrofuran solution was combined with the filtrate from the reaction mixture and reduced to dryness in vacuo. The solid residue was crystallized from acetone and identified as 1-n-propyl-2-(methylthio)-4,5-bis(hydroxymethyl)imidazole (48% yield).

Provenance & Evidence