Water → 2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxaldehyde

HRID 487192ノート

反応式

HRID 487192 の反応式
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[CH:18]=[C:19](CO)[CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[C:24]1(C)C=CC=CC=1.[OH2:31]>[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[C:18]([CH:24]=[O:31])=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 962WaterHCID 1140TolueneHCID 190942372-n-butyl-1-(2-chlorophenyl)methyl-6-hydroxymethyl-1H-benzimidazole

生成物 1

HCID 190942612-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxaldehyde収率 66%

試薬・触媒・溶媒 1

HCID 178418406HCID 178418406、化合物触媒

実験手順

A suspension of 2-n-butyl-1-(2-chlorophenyl)methyl-6-hydroxymethyl-1H-benzimidazole (1 g, 3.04 mmol, prepared in Example 9(i)), toluene (500 mL) and activated manganese dioxide (4 g) was refluxed with a Dean-Stark water separator for 4 hours. The mixture was filtered hot, concentrated and the crude product was treated with celite in methylene chloride to afford, after concentration, a residue that crystallized. Recrystallization from hexane gave 0.65 g (66%) of 2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-benzimidazole-7-carboxaldehyde; mp 113.5°-115° C.

後処理

  1. filtrationThe mixture was filtered hot
  2. concentrationconcentrated
  3. additionthe crude product was treated with celite in methylene chloride
  4. customto afford
  5. concentrationafter concentration
  6. customa residue that crystallized
  7. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-d0761cf341624c80aec6bb44c43bd7ec
出典データセット
uspto-grants-1994_03
特許番号
US05294631

反応ノート

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