Triethylamine → HCID 13603537, compound

Temperature

0 °C

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.

1. customIn a round bottom flask equipped with a magnetic stirrer, ice bath, addition funnel
2. additionwas added dropwise at a rate such that the temperature
3. customremained below 10° C
4. temperatureto warm to room temperature
5. customThe layers were separated
6. dry with materialthe organic layer was dried over MgSO4
7. filtrationwas immediately filtered into an addition funnel
8. customfitted to a round bottom flask
9. additionThe solution was added relatively quickly at room temperature and after 1 hour
10. customthe layers were separated
11. washthe organic layer was washed again with water (1×250 ml)
12. dry with materialwas dried over MgSO4
13. customThe solvents were stripped on a rotary evaporator
14. customto leave a solid, 13.2 g, 80.4% yield
15. customThis was recrystallized by the cloud point method
16. customto give pure product, mp 129°-132° C

ORD record

ord-f2b1e4e744104fa68688cc8a49726fdb

Source dataset

uspto-grants-1986_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04576629