Water → 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-cyanoethyl)phenyl]butanamide

HRID 35026

반응식

HRID 35026 반응식
[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]Br)=[CH:8][CH:7]=1)=[O:4].[C-:23]#[N:24].[Na+].O>CS(C)=O>[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:23]#[N:24])=[CH:8][CH:7]=1)=[O:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium Cyanide2회HCID 212977022,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide

생성물 1

HCID 212977082,2,3,3,4,4,4-heptafluoro-N-[4-(2-cyanoethyl)phenyl]butanamide수율 49.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide (9.9 g), and sodium cyanide (1.72 g) in dimethylsulfoxide (50 mL) was stirred at room temperature under a nitrogen atmosphere for 24 hours. The mixture was treated with additional sodium cyanide (0.8 g) and the reaction was stirred for another 18 hours. The reaction mixture was poured into water (1 L) and extracted with diethyl ether. The extracts were washed with water and with saturated brine solution, dried over sodium sulfate, filtered and concentrated with a rotary evaporator. The crude orange residue was chromatographed on silica gel, eluted with a hexane-ethylacetate (7:3) mixture to give 4.2 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-cyanoethyl)phenyl]butanamide as a yellow solid.

후처리

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with water and with saturated brine solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated with a rotary evaporator
  6. customThe crude orange residue was chromatographed on silica gel
  7. washeluted with a hexane-ethylacetate (7:3) mixture

출처 및 근거

ORD 기록
ord-9448df8c85814fb8925098fb336fbef3
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764623

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