Methanesulfonyl chloride → N-(4-Cyano-2-iodo-5-(trifluoromethyl)phenyl)methanesulfonamide

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile (8.04 g, 25.77 mmoles) was dissolved in anhydrous THF (60 mL), stirred under a nitrogen atmosphere and cooled in an ice/brine bath for 20 min. 1.0 M potassium tert-butoxide in THF (82 mL, 82 mmoles) was added and the reaction mixture was stirred for 20 min. Methanesulfonyl chloride (3.2 mL, 41.18 mmoles) was then added and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was quenched with 1N HCl (90 mL) and extracted with dichloromethane (3×100 mL). The organic extracts were diluted with diethyl ether and a white solid precipitated. The solid was filtered, washed and dried to yield the title compound. The filtrate was concentrated to a crude orange solid. The compound was purified by column chromatography (SiO2, 100% CH2Cl2).

1. temperaturecooled in an ice/brine bath for 20 min
2. stirringthe reaction mixture was stirred for 20 min
3. stirringthe reaction mixture was stirred at ambient temperature overnight
4. customThe reaction mixture was quenched with 1N HCl (90 mL)
5. extractionextracted with dichloromethane (3×100 mL)
6. additionThe organic extracts were diluted with diethyl ether
7. customa white solid precipitated
8. filtrationThe solid was filtered
9. washwashed
10. customdried

ORD record

ord-62fd9ef8f9a84f1cb3b2b0ccb487b9d7

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394971B2