1h-Benzimidazole-6-methanol,1-[(2-chlorophenyl)methyl]-2-methyl- → 1h-Benzimidazole-6-carbaldehyde,1-[(2-chlorophenyl)methyl]-2-methyl-

HRID 276037Notes

Reaction equation

HRID 276037 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:16]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:16]

Participants

4

Reactant 1

HCID 183155381h-Benzimidazole-6-methanol,1-[(2-chlorophenyl)methyl]-2-methyl-

Product 1

HCID 186811111h-Benzimidazole-6-carbaldehyde,1-[(2-chlorophenyl)methyl]-2-methyl-Yield 97.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Manganese dioxide (3.46 g) was added to a solution of 3.46 g of 1-(2-chlorobenzyl)-6-hydroxymethyl-2-methylbenzimidazole in 100 ml of toluene, and toluene was heat-refluxed for 3.5 hours while the mixture was dehydrated using a molecular sieve 4A. The solid material was separated through filtration, and was washed with chloroform. The filtrate was concentrated to give 3.35 g of 1-(2-chlorobenzyl)-6-formyl-2-methylbenzimidazole.

Workup

  1. temperaturewas heat-refluxed for 3.5 hours while the mixture
  2. customThe solid material was separated through filtration
  3. washwas washed with chloroform
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-53b308a40bd24c668bcafd9c2300909b
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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