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

HRID 487192노트

반응식

HRID 487192 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 178418406HCID 178418406, 화합물촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0761cf341624c80aec6bb44c43bd7ec
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294631

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