Bromochloromethane → HCID 10241417, compound

2-Mercapto-5-methyl-1,3,4-thiadiazole (41.4 g, 313 mmol) was added to an ice-bath cooled (5° C.) aqueous solution of 85% KOH (20.7 g, 313 mmol) in EtOH (160 mL). The ice bath was removed and the mixture stirred until complete dissolution occurred (30 min). The solvent was then evaporated to leave a viscous oil which solidified. The resulting potassium salt was dissolved in CH3CN (200 mL), and the solution was cooled in an ice bath and treated with bromochloromethane (121 g, 939 mmol). The ice in the bath was allowed to melt and the mixture was further stirred at R.T. for 25 h. The reaction mixture was partitioned between EtOAc and H2O. The organic phase was dried (MgSO4) and evaporated. The residue was purified by passing through a pad of silica gel, eluted first with CH2Cl2 and then with 5% CH3CN/CH2Cl2 to afford 93.0 g (76.0%) of 2-[(chloromethyl)-thio]-5-methyl-1,3,4-thiadiazole.

1. customThe ice bath was removed
2. custom(30 min)
3. customThe solvent was then evaporated
4. customto leave a viscous oil which
5. temperaturethe solution was cooled in an ice bath
6. stirringthe mixture was further stirred at R.T. for 25 h
7. customThe reaction mixture was partitioned between EtOAc and H2O
8. dry with materialThe organic phase was dried (MgSO4)
9. customevaporated
10. customThe residue was purified
11. washeluted first with CH2Cl2

ORD record

ord-6a96135823de435d8d6e3fcbd2206951

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116833