5,6-Dimethylbenzimidazole → 1-(3-Hydroxypropyl)-5,6-dimethylbenzimidazole

HRID 1653993Notes

Reaction equation

HRID 1653993 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][OH:18].O>CN(C)C=O>[OH: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

6

Reactant 4

HCID 6755,6-DimethylbenzimidazoleHCID 962WaterHCID 123133-Chloro-1-propanolHCID 24758Sodium hydride

Product 1

HCID 200789601-(3-Hydroxypropyl)-5,6-dimethylbenzimidazole

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 0.76 g of NaH, the mixture was stirred at room temperature for 30 minutes. To the mixture was added dropwise 5 ml of 3-chloro-1-propanol, and the reaction was carried out by stirring at room temperature for 2 days, followed by an addition of water to stop the reaction. Subsequently, according to the same processes as in Example 1, crude 1-(3-hydroxypropyl)-5,6-dimethylbenzimidazole was obtained. The conversion to this compound from 5,6-dimethylbenzimidazole was found to be 90%.

Workup

  1. stirringby stirring at room temperature for 2 days
  2. customthe reaction

Sources & evidence

ORD record
ord-331ff00f5f834baa831d6c23ca3f5f59
Source dataset
uspto-grants-1995_04
Patent number
US05405839

Reaction notes

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