Dichloromethane → HCID 14769542, compound

Temperature

40 °C

To a mixture of methyl 5-formamido-1,2,4-thiadiazole-3-carboxylate (9.2 g) and methyl methylthiomethyl sulfoxide (6.1 g) in N,N-dimethylformamide (100 ml) was added 50% sodium hydride (7.1 g) with cooling in an ice-bath. The mixture was stirred for an hour at ambient temperature and for an additional one hour at 40° C. After cooling to ambient temperature, methylene chloride (300 ml) was added to the reaction mixture, and the resulting precipitates were collected by filtration and washed with methylene chloride. The precipitates were added to a stirred mixture of hydrochloric acid (14.7 ml), ice-water (200 ml) and methylene chloride (200 ml). An insoluble material was filtered off and the methylene chloride layer was separated from the filtrate. The solution was dried over anhydrous magnesium sulfate, evaporated and the residue was triturated with diethyl ether to give the title compound (4.5 g), mp. 130° to 132° C.

1. temperaturewith cooling in an ice-bath
2. temperatureAfter cooling to ambient temperature
3. customthe resulting precipitates
4. filtrationwere collected by filtration
5. washwashed with methylene chloride
6. additionThe precipitates were added to a stirred mixture of hydrochloric acid (14.7 ml), ice-water (200 ml) and methylene chloride (200 ml)
7. filtrationAn insoluble material was filtered off
8. customthe methylene chloride layer was separated from the filtrate
9. dry with materialThe solution was dried over anhydrous magnesium sulfate
10. customevaporated
11. customthe residue was triturated with diethyl ether

ORD record

ord-fd540f6546c944d8bcd307f2cc754d4e

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04585872