5,6-Dimethylbenzimidazole → 4-(5,6-Dimethyl-1h-benzo[d]imidazol-1-yl)butan-1-ol

HRID 1653995Notes

Reaction equation

HRID 1653995 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[H-].[Na+].Cl[CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>CN(C)C=O>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][N:6]1[C:5]2[CH:9]=[C:10]([CH3:11])[C:2]([CH3:1])=[CH:3][C:4]=2[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 6755,6-DimethylbenzimidazoleHCID 135694-Chloro-1-butanol2×HCID 24758Sodium hydride2×

Product 1

HCID 200789574-(5,6-Dimethyl-1h-benzo[d]imidazol-1-yl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.46 g of 5,6-dimethylbenzimidazole dissolved in 50 ml of dry N,N-dimethylformamide was added 0.9 g of NaH, the mixture was stirred at room temperature for 30 minutes, 8 ml of 4-chloro-1-butanol was added dropwise, and after stirring at room temperature for one day, 0.65 g of NaH and 2 ml of 4-chloro-1-butanol were further added to carry out the reaction for 8 days. Following the same processes as in Example 1, crude 1-(4-hydroxybutyl)-5,6-dimethylbenzimidazole was obtained. The conversion to this compound from 5,6-dimethylbenzimidazole was found to be 50%.

Workup

  1. stirringafter stirring at room temperature for one day
  2. customthe reaction for 8 days

Sources & evidence

ORD record
ord-bd3ca50e1a494759b4f4b8664795d9e4
Source dataset
uspto-grants-1995_04
Patent number
US05405839

Reaction notes

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