반응 #63298

반응 방정식

4-aminobenzonitrile

triethylamine

perfluorobutyryl chloride

→

2,2,3,3,4,4,4-heptafluoro-N-[4-(cyano)phenyl]butanamide

수율 36.9%

용매

dichloromethane

dichloromethane

HCl

반응 조건

후처리

1. 1
   온도was cooled in ice under a nitrogen atmosphere
2. 2
   기타the layers were partitioned in a separatory funnel
3. 3
   세척The organic phase was washed with a saturated brine solution
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated with a rotary evaporator
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
8. 8
   기타Upon dilution with hexane the product precipitated

실험 절차

A mixture of 4-aminobenzonitrile (1.58 g), triethylamine (1.36 g), and dichloromethane (20 mL) was cooled in ice under a nitrogen atmosphere. To this mixture was added perfluorobutyryl chloride (3.11 g) in dichloromethane (10 mL) and the resulting mixture was allowed to warm to room temperature and was then stirred for three hours. The reaction mixture was diluted with HCl solution (1N, 50 mL) and the layers were partitioned in a separatory funnel. The organic phase was washed with a saturated brine solution, dried over MgSO4, filtered and concentrated with a rotary evaporator. The residue was dissolved in dichloromethane. Upon dilution with hexane the product precipitated to give 1.55 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(cyano)phenyl]butanamide, m.p. 116°-118° C.

출처