Sodium hydride → Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonate

HRID 273832노트

반응식

HRID 273832 반응식
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].Cl.[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28](CCl)=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]>CN(C)C=O>[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28]([C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:6]([O:5][CH2:4][CH3:3])=[O:7])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 69090Diethyl 2-benzylpropanedioateHCID 193515432-n-butyl-1-(2-chlorophenyl)methyl-5chloromethyl-1H-imidazole hydrochloride

생성물 1

HCID 57500985Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonate수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To dry dimethylformamide (50 mL) under argon was added sodium hydride (0.53 g, 0.022 mol) followed by diethyl benzyl malonate (5.51 g, 0.022 mol) in dimethylformamide (10 mL) at 0° C. The mixture was stirred at ambient temperature for one hour. A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-chloromethyl-1H-imidazole hydrochloride (3.5 g, 0.0105 mol) in dimethylformamide (40 mL) was added over 5 minutes. The reaction mixture was stirred at 25° C. for 18 hours, then partitioned between water and methylene chloride. The organic layer was washed with water, dried, and concentrated. The crude product was flash chromatographed over silica gel to give 4.54 g (85%) of the title compound as an oil.

후처리

  1. stirringThe reaction mixture was stirred at 25° C. for 18 hours
  2. custompartitioned between water and methylene chloride
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed over silica gel

출처 및 근거

ORD 기록
ord-bdbec6a41e7446658978f32b0c1ff3f2
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387601

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