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Water → 4-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazole

HRID 969528
ノート
印刷プレビュー

反応式

HRID 969528 の反応式
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[NH:14][C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:23][O:24][CH3:25].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:23][O:24][CH3:25])[C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 672202147-(benzyloxy)-5-bromo-2-methyl-1H-benzo[d]imidazole

生成物 1

HCID 691352384-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazole収率 26.4%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

2.0 g (6.3 mmol) 4-Benzyloxy-6-bromo-2-methyl-1H-benzimidazole were solved in dimethylformamide (10 ml) and the solution was cooled to 0° C. 151 mg (6.5 mmol) sodium hydride (60%) were added in portions and the reaction was stirred for 20 min. 435 μl (6.3 mmol) 1-Chloro-1-methoxy-methane were added and the reaction was stirred at 0° C. After 2 h the mixture was poured into water (200 ml) and extracted with ethyl acetate. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=6:1) to afford 0.6 g (26%) of the title compound as a yellow oil.

後処理

  1. stirringthe reaction was stirred at 0° C
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=6:1)

出典と根拠

ORDレコード
ord-0e4e6c3d99c64eb5bf8d5d65fa1fc9d2
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07307084B2

反応ノート

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