Sodium Cyanide → [2-(4-Isopropyl-phenyl)-thiazol-4-yl]-acetonitrile

HRID 394239

反応式

HRID 394239 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[S:6][CH:7]=1.C(C1C=CC([C:24]([NH2:26])=S)=CC=1)(C)C.ClCC(CCl)=O.[C-]#N.[Na+]>CS(C)=O.O>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[S:6][CH:7]=[C:3]([CH2:2][C:24]#[N:26])[N:4]=2)=[CH:9][CH:10]=1)([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 8929Sodium CyanideHCID 107931,3-DichloroacetoneHCID 20788314-(Propan-2-yl)benzene-1-carbothioamideHCID 20956974-Chloromethyl-2-(4-isopropyl-phenyl)-thiazole

生成物 1

HCID 22647623[2-(4-Isopropyl-phenyl)-thiazol-4-yl]-acetonitrile収率 96%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

14.5 g (57.6 mmol) of 4-chloromethyl-2-(4-isopropyl-phenyl)-thiazole (prepared from 4-isopropyl-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) and 4.08 g (83.4 mmol) of sodium cyanide in 50 ml of dimethyl sulfoxide were stirred at 40° C. for 2 hours. Then, the reaction mixture was poured into a mixture of ice and water and was subsequently extracted with 3 portions of 75 ml of tert-butyl methyl ether. The combined organic phases were washed with water, then with brine and dried with anhydrous sodium sulfate. After evaporation of the solvent, 13.4 g (96% of theory) of [2-(4-isopropyl-phenyl)-thiazol-4-yl]-acetonitrile were obtained as brown solid.

後処理

  1. extractionwas subsequently extracted with 3 portions of 75 ml of tert-butyl methyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialwith brine and dried with anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

出典と根拠

ORDレコード
ord-6febcf5681e248c295525a601d837e59
出典データセット
uspto-grants-2004_10
特許番号
US06809110B2

関連ノート

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