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

HRID 1416022노트

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HRID 1416022 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
72.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c7e86dd6c2b431e99e30a2f0635c7bf
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910506

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