Imidazole → 3-(1-Imidazolyl)-benzaldehyde dimethyl acetal

HRID 1275826노트

반응식

HRID 1275826 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][CH:10]([O:18][CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1>CN(C)C=O.O.[Cu]>[CH3:19][O:18][CH:10]([O:9][CH3:8])[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:16]=1

참가 물질

7

반응물 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 1053951-Bromo-3-(dimethoxymethyl)benzene

생성물 1

HCID 221178243-(1-Imidazolyl)-benzaldehyde dimethyl acetal수율 79.4%

시약·촉매·용매 3

HCID 23978Copper촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
155 °C

실험 절차

A solution of 296 mg of imidazole and 131 mg of sodium hydride (80% dispersion in mineral oil) in 2 ml of anhydrous dimethylformamide was stirred at room temperature for 1 hour under nitrogen. 1.0 g of 3-bromobenzaldehyde dimethyl acetal and 30 mg copper powder were then added and the mixture was stirred at 150-160° C. under nitrogen for 36 hours. The cooled mixture was diluted with 20 ml of water and extracted with four 25 ml portions of dichloromethane. The combined extracts were washed with two 25 ml portions of 25% aqueous ammonia, followed by two 25 ml portions of brine and then dried over anhydrous magnesium sulphate. The solution was concentrated under reduced pressure to give 0.75 g of 3-(1-imidazolyl)-benzaldehyde dimethyl acetal as a clear viscous oil.

후처리

  1. extractionextracted with four 25 ml portions of dichloromethane
  2. washThe combined extracts were washed with two 25 ml portions of 25% aqueous ammonia
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationThe solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e0c86e482b784b8e82c1f4b89794bd98
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162918

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