Dichloromethane → 1H-Imidazole-2-acetonitrile, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-

HRID 1416022ノート

反応式

HRID 1416022 の反応式
Cl[CH2:2][C:3]1[N:4]([CH3:20])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[C-:21]#[N:22].[K+].C(Cl)Cl>CN(C)C=O>[Cl:19][C:14]1[CH:13]=[C:12]([S:11][C:5]2[N:4]([CH3:20])[C:3]([CH2:2][C:21]#[N:22])=[N:7][C:6]=2[CH:8]([CH3:10])[CH3:9])[CH:17]=[C:16]([Cl:18])[CH:15]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 221306052-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole

生成物 1

HCID 4740091H-Imidazole-2-acetonitrile, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
72.5 °C

実験手順

In 13.6 ml of dry dimethylformamide was dissolved 4.75 g (13.6 mmol)of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (28a)and 1.0 g of potassium cyanide (97.5%), and the mixture was stirred with heating at 70 to 75° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and to the residue, water was added. The mixture was extracted with diethyl ether, and the organic layer was washed with water 3 times and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:9 to 4)to obtain 2.43 g of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetonitrile (Compound I-80a)(yield 53%). mp 103-105° C.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue, water was added
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe organic layer was washed with water 3 times
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-9c7e86dd6c2b431e99e30a2f0635c7bf
出典データセット
uspto-grants-1999_06
特許番号
US05910506

反応ノート

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