1-Methylimidazole → HCID 131710733, compound

Participants

Reaction Steps

A solution of 13.7 g of ethyl chlorothiolformate in 50 ml of dry tetrahydrofuran was added to 9.0 g of 1-methylimidazole in 200 ml of dry tetrahydrofuran at 5°, over a 20-minute period. The mixture was stirred at 5° for 30 minutes, then 16.0 g of 31B was added all at once, and the stirred mixture was allowed to slowly warm to room temperature and was stirred overnight. The solvent was stripped, the residue dissolved in a mixture of water and methylene chloride. The two phases were separated, the water phase was extracted with methylene chloride, the methylene chloride solutions were combined, dried (MgSO4), filtered and the solvent evaporated under reduced pressure, to leave an oil. The oil was stirred with a mixture of water and ether; solid material was filtered off and recrystallized from ethyl alcohol to give nitro(tetrahydro-2H-1,3-thiazin-2-ylidene ethanethioic acid, S-ethyl ester (31C) as a pale yellow solid, m.p.: 124°-124.5°.

Provenance & Evidence