Ethanethiol → 4-(2,4-Dichlorophenyl)-2-ethylthiobenzonitrile

HRID 1635724ノート

反応式

HRID 1635724 の反応式
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].[H][H].F[C:9]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]>CN(C)C=O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:15]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([S:5][CH2:3][CH3:4])[CH:16]=1

参加物

6

反応物 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 221708972-Fluoro-4-(2,4-dichlorophenyl)benzonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 221709574-(2,4-Dichlorophenyl)-2-ethylthiobenzonitrile収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

0.12 g (3.0 mmol) of 60% sodium hydride was stirred in 30 ml of N,N-dimethylformamide at room temperature while 0.2 g (3.2 mmol) of ethanethiol was added dropwise. After generation of hydrogen was over, 0.7 g (2.6 mmol) of 2-fluoro-4-(2,4-dichlorophenyl)benzonitrile was added, and the reaction mixture was stirred at 60° C. for 6 hours. The reaction mixture was poured into about 100 ml of ice-cold water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.7 g of 4-(2,4-dichlorophenyl)-2-ethylthiobenzonitrile (yield 88.0%) as pale yellow crystals (m.p. 89-92° C.).

後処理

  1. additionwas added dropwise
  2. additionwas added
  3. extractionextracted with 50 ml of ethyl acetate twice
  4. washThe ethyl acetate layer was washed with 50 ml of water twice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe ethyl acetate was distilled off under reduced pressure
  7. customPurification of the residue by silica gel column chromatography

出典と根拠

ORDレコード
ord-e9581238564b41fd9597428d7964acd6
出典データセット
uspto-grants-2003_01
特許番号
US06509354B1

反応ノート

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