Hydrochloric Acid → HCID 15453204, compound

Temperature

2.5 °C

A solution of 5-amino-4-bromo-3-methylisoxazole (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5° C. After stirring at 0-5° C. for 10 min, the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0° C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min at 0-5° C. Excess sodium hydride was decomposed by the addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170° C. (dec.).

1. temperaturethe reaction was warmed to room temperature for 10 min.
2. customthe reaction
3. temperatureThe reaction mixture was re-cooled to 0° C.
4. stirringStirring
5. waitwas continued for 20 min at 0-5° C
6. extractionextracted with dichloromethane
7. dry with materialThe extract was dried over anhydrous magnesium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-a168e7a6980f41f78ef9976c777e115a

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06030991