Stannous Chloride → 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole

HRID 244468

反応式

HRID 244468 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9](=O)[CH3:10])=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:9]([CH3:10])=[N:19][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 59437302N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide

生成物 1

HCID 594373055-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole収率 25.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a stirred room temperature solution of N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide (3.7 g, 10.8 mmol) in ethanol (75 mL) was added tin (II) chloride (6 g, 31.4 mmol) and the mixture was warmed at 90° C. After 3 hours, the mixture was cooled, concentrated in vacuo, diluted with cold water, made basic with 2 N NaOH (pH 11), and extracted with three 75 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a reddish brown oil. The residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride to afford 830 mg of 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole as an off-white solid.

後処理

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with cold water
  4. extractionextracted with three 75 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a reddish brown oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride

出典と根拠

ORDレコード
ord-269ac4b146d64aeabcef2f6db67097bf
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

関連ノート

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