Sodium Hydroxide → 1-Methanesulphonyl-3-(2,2,2-trifluoroethyl)thiourea

A solution of 2,2,2-trifluoroethylisothiocyanate (1.4 g.) in acetone (20 ml.) was added to a solution of methanesulphonamide (0.95 g.) and sodium hydroxide (0.44 g.) in water (10 ml.) and the mixture stirred and heated under reflux for 18 hours, and then evaporated to dryness. The residue was dissolved in water and the solution washed with ethyl acetate and then acidified with concentrated hydrochloric acid. The mixture was extracted three times with ethyl acetate and the combined extracts dried and evaporated to dryness. The residue was triturated with acetonitrile and filtered and the filtrate evaporated to dryness. The residue was dissolved in ether, and the solution extracted with aqueous sodium bicarbonate solution. The extract was neutralised with N hydrochloric acid and the mixture extracted with ethyl acetate. The ethyl acetate extract was dried and evaporated to dryness to give 1-methanesulphonyl-3-(2,2,2-trifluoroethyl)thiourea (0.45 g.) which was used without further purification.

1. temperatureheated
2. temperatureunder reflux for 18 hours
3. customevaporated to dryness
4. dissolutionThe residue was dissolved in water
5. washthe solution washed with ethyl acetate
6. extractionThe mixture was extracted three times with ethyl acetate
7. customthe combined extracts dried
8. customevaporated to dryness
9. customThe residue was triturated with acetonitrile
10. filtrationfiltered
11. customthe filtrate evaporated to dryness
12. dissolutionThe residue was dissolved in ether
13. extractionthe solution extracted with aqueous sodium bicarbonate solution
14. extractionthe mixture extracted with ethyl acetate
15. extractionThe ethyl acetate extract
16. customwas dried
17. customevaporated to dryness

ORD record

ord-b9627e2ab1d24354b37df860e936bbd0

Source dataset

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04762932