Benzyl Bromide → 2-Benzyloxymethyl-1-(3,5-dichloro-benzyl)-1H-imidazole

HRID 2101510노트

반응식

HRID 2101510 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][OH:14].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:14][CH2:13][C:9]1[N:8]([CH2:7][C:6]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:4]([Cl:3])[CH:5]=2)[CH:12]=[CH:11][N:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 57801498[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol

생성물 1

HCID 119512412-Benzyloxymethyl-1-(3,5-dichloro-benzyl)-1H-imidazole수율 5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

To NaH in DMF, was added [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-methanol (see Example 1) in DMF. The reaction mixture was stirred at 40° C. for 30 min and benzyl bromide was dropwise added. The reaction mixture was stirred at 40° C. for another 3 h. The mixture was diluted with EtOAc and washed with water, 1N HCl and saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 98:2 as an eluent to afford the title compound (7 mg, 5%); MS m/z 347 [C18H16Cl2N2O+H]+.

후처리

  1. stirringThe reaction mixture was stirred at 40° C. for another 3 h
  2. washwashed with water, 1N HCl and saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel preparative TLC

출처 및 근거

ORD 기록
ord-3046409271b84e10b6d14775e033c287
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572921B2

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