تفاعل #84241

معادلة التفاعل

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile

potassium tert-butoxide

Methanesulfonyl chloride

→

title compound

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in an ice/brine bath for 20 min
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 20 min
3. 3
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature overnight
4. 4
   أخرىThe reaction mixture was quenched with 1N HCl (90 mL)
5. 5
   استخلاصextracted with dichloromethane (3×100 mL)
6. 6
   workup.ADDITIONThe organic extracts were diluted with diethyl ether
7. 7
   أخرىa white solid precipitated
8. 8
   ترشيحThe solid was filtered
9. 9
   غسيلwashed
10. 10
    أخرىdried

الإجراء التجريبي

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).

المصدر