Isopropanol → HCID 178473692, compound

2,5-Dimercapto-1,3,4-thiadiazole (DMTD) (276.21 g, 1.84 mol) and isopropanol (400 ml) were charged to a reaction flask fitted with a reflux condenser. Propylene oxide (22.8 g, 3.84 mol) was added, with stirring, at a rate to maintain reflux. The reaction was stirred for 15 min. and then solvent was stripped under reduced pressure by rotary evaporation. This intermediate product (157.5 g, 0.592 mol), water (100 ml) and sodium hydroxide (23.7 g) were charged to a reaction flask and stirred until homogenous. Unreacted material was extracted with ether (200 ml) and additional water (200 ml). The water layer was acidified and extracted with diethyl ether (200 ml). The ether layer was separated and washed with water (200 ml). The acidified ether extract was dried over magnesium sulfate and filtered. The solvent was removed by rotary evaporation under reduced pressure. A yield of 99.2 g. was obtained.

1. customfitted with a reflux condenser
2. temperatureto maintain
3. temperaturereflux
4. stirringThe reaction was stirred for 15 min.
5. customsolvent was stripped under reduced pressure by rotary evaporation
6. stirringstirred until homogenous
7. extractionUnreacted material was extracted with ether (200 ml) and additional water (200 ml)
8. extractionextracted with diethyl ether (200 ml)
9. customThe ether layer was separated
10. washwashed with water (200 ml)
11. extractionThe acidified ether extract
12. dry with materialwas dried over magnesium sulfate
13. filtrationfiltered
14. customThe solvent was removed by rotary evaporation under reduced pressure
15. customwas obtained

ORD record

ord-eef8ea180a5b416da4ea79bc028b26ff

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04935157