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

HRID 35026

反応式

HRID 35026 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium Cyanide2 回HCID 212977022,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9448df8c85814fb8925098fb336fbef3
出典データセット
uspto-grants-1988_08
特許番号
US04764623

関連ノート

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