Triethylamine → HCID 13603537, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask equipped with a magnetic stirrer, ice bath, addition funnel and nitrogen atmosphere were mixed 2-thiophene carbinol (6.0 g, 0.05 mol), dichloromethane (100 ml) and triethyl amine (6.6 g, 0.065 mol). The reaction was cooled to 0° C. and thionyl chloride (7.14 g, 0.06 mol) diluted with dichloromethane (10 ml) was added dropwise at a rate such that the temperature remained below 10° C. The reaction was then allowed to warm to room temperature, was mixed in a large beaker with water (120 ml) and was neutralized by the addition of solid sodium bicarbonate to pH=7. The layers were separated; the organic layer was dried over MgSO4 and was immediately filtered into an addition funnel fitted to a round bottom flask charged with dichloromethane (100 ml), 1-methyl-4-hydroxy-3-[5-mercapto-1,3,4-thiadiazol-2-yl]urea (12.8 g, 0.055 mol) and triethylamine (6.6 g, 0.065 mol). The solution was added relatively quickly at room temperature and after 1 hour, water (150 ml) was added to the reaction; the layers were separated, and the organic layer was washed again with water (1×250 ml) and was dried over MgSO4. The solvents were stripped on a rotary evaporator to leave a solid, 13.2 g, 80.4% yield. This was recrystallized by the cloud point method using ethylacetate and hexane to give pure product, mp 129°-132° C. IR: (KBr) 1700, 1500, 1430, 1400, 1390, 1360, 1340, 1300, 1280, 1210, 1100, 1010, 900, 700.

Provenance & Evidence