Diethylcarbamoyl chloride → HCID 19762011, compound

To a flask was added 17.17 g of 1,2,4-triazole-3-thiol and 200 ml of dry tetrahydrofuran. The mixture was stirred under nitrogen at room temperature and 43 ml of diethylcarbamoyl chloride was quickly added dropwise. The mixture was cooled to between 0° C. and 5° C. Dimethylaminopyridine, one gram, was added followed by the slow dropwise addition of 47.4 ml of triethyl amine while maintaining the reaction temperature between 0° C. and 5° C. until all the triethyl amine was added. The mixture became thick and was allowed to warm to room temperature, then was refluxed at 70° C. for about 20 minutes. After the mixture was cooled to room temperature, the volatiles were evaporated off to leave an oily residue. Water, 100 ml, was added to the residue which was then extracted twice with 100 ml portions of ethyl acetate. The ethyl acetate layer was dried using magnesium sulfate and concentrated to a pale yellow solid which was dried thoroughly under vacuum to yield 31.03 g of pale yellow solid.

1. temperatureThe mixture was cooled to between 0° C. and 5° C
2. additionwas added
3. temperatureto warm to room temperature
4. temperaturewas refluxed at 70° C. for about 20 minutes
5. temperatureAfter the mixture was cooled to room temperature
6. customthe volatiles were evaporated off
7. customto leave an oily residue
8. extractionwas then extracted twice with 100 ml portions of ethyl acetate
9. dry with materialThe ethyl acetate layer was dried
10. concentrationconcentrated to a pale yellow solid which
11. customwas dried thoroughly under vacuum

ORD record

ord-e3be5df152854e5bbedda82daea95cf0

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05211739