Dimethyl Sulfoxide → HCID 14835682, compound

Under nitrogen atmosphere, to a solution of oxalyl chloride (3.78 mL, 44.6 mmol) in dichloromethane (20 mL) was added dimethyl sulfoxide (4.75 mL, 66.9 mmol) at −78° C. and the mixture was stirred for 30 min. To the reaction mixture was added (2-methyl-1,3-benzothiazol-7-yl)methanol (4.00 g, 22.3 mmol) at −78° C. and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (18.8 mL, 134 mmol) at −78° C. and the mixture was stirred for 30 min. The reaction mixture was warmed to room temperature, and the mixture was further stirred at room temperature for 4 hr. Saturated aqueous ammonium chloride solution was added and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (dichloromethane/hexane) to give the title compound (3.54 g, yield 90%).

1. stirringthe mixture was stirred for 2 hr
2. stirringthe mixture was stirred for 30 min
3. stirringthe mixture was further stirred at room temperature for 4 hr
4. extractionthe mixture was extracted with dichloromethane
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by recrystallization (dichloromethane/hexane)

ORD record

ord-52186e1f45cd4953b1c5c33d5a7db84b

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110585B2