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

HRID 2101510ノート

反応式

HRID 2101510 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-3046409271b84e10b6d14775e033c287
出典データセット
uspto-grants-2009_08
特許番号
US07572921B2

反応ノート

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