Thiophenol → HCID 15593669, compound

In one portion 2.5 g of trimethylamine was added to a solution of 4.6 g of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one in 75 ml of ethyl ether in a 250 ml flask. A solution of 2.8 g of thiophenol in 25 ml of ethyl ether was then added dropwise to the flask during a 15 minute period. The reaction was allowed to stir for 3 hrs. after which it was filtered. The filter cake was washed with ether, and the filter cake was discarded. Successively, the ether solution was washed twice with 50 ml of water and once with 50 ml of saturated sodium chloride solution. The ether solution was then dried over anhydrous sodium sulfate. The ether was evaporated, leaving a solid residue which was recrystallized from 75 ml of cyclohexane. The yellow-orange 3-chloro-5-phenylthio-4H-1,2,6-thiadiazin-4-one weighed 3.6 g, mp 99.5°-101.5° C. (Lit. mp 102.5°-103.5° C, J. Geevers and W. P. Trompen, supra.). The ir spectrum was consistent with the assigned structure.

1. filtrationafter which it was filtered
2. washThe filter cake was washed with ether
3. washSuccessively, the ether solution was washed twice with 50 ml of water and once with 50 ml of saturated sodium chloride solution
4. dry with materialThe ether solution was then dried over anhydrous sodium sulfate
5. customThe ether was evaporated
6. customleaving a solid residue which
7. customwas recrystallized from 75 ml of cyclohexane

ORD record

ord-8eccee9e2971487197f948ddd7ec2406

Source dataset

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04100281