Propionitrile → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 47880

反応式

HRID 47880 の反応式
[C:1](#[N:4])CC.Cl[C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1.[C-]#N.[Na+]>CN(C)C1C=CN=CC=1.O>[Cl:12][C:11]1[C:6]([C:1]#[N:4])=[N:7][CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:10]=1

参加物

6

反応物 3

HCID 7854PropionitrileHCID 8929Sodium CyanideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

生成物 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile収率 73%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒2 回

反応条件

温度
15 °C

実験手順

Propionitrile (656 ml), 2,3-dichloro-5-trifluoromethylpyridine (87.5 g) and 4-dimethylaminopyridine (52 g) were heated at reflux for 5 hours under nitrogen. The mixture was cooled and a solution of sodium cyanide (30 g) in water (110 ml) added at 15° C. After stirring at 15° C. for 5 hours the reaction was complete and water (250 ml) added to dissolve the inorganic salts. The organic phase was washed with water followed by extraction with 2N HCl to remove 4-dimethylaminopyridine. Propionitrile was removed by vacuum distillation at 40° C. to give the product, 3-chloro-2-cyano-5-trifluoromethylpyridine in 73 to 84% yield.

後処理

  1. temperatureat reflux for 5 hours under nitrogen
  2. temperatureThe mixture was cooled
  3. dissolutionto dissolve the inorganic salts
  4. washThe organic phase was washed with water
  5. extractionfollowed by extraction with 2N HCl
  6. customto remove 4-dimethylaminopyridine
  7. customPropionitrile was removed by vacuum distillation at 40° C.

出典と根拠

ORDレコード
ord-2759955b5a064331b73b1134fed2a2e3
出典データセット
uspto-grants-2004_03
特許番号
US06699993B1

関連ノート

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