Water → 5-Hydroxymethyl-2-(2'-methoxy-4'-methanesulfonylamino-phenyl)benzimidazole

HRID 2309911Notes

Reaction equation

HRID 2309911 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:13]=3[O:23][CH3:24])[NH:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:2][CH2:3][C:5]1[CH:26]=[CH:25][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:13]=3[O:23][CH3:24])[NH:11][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20184489HCID 20184489, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 201845615-Hydroxymethyl-2-(2'-methoxy-4'-methanesulfonylamino-phenyl)benzimidazoleYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A quantity of 1.9 gm (5.1 mmol) of 5-methoxycarbonyl-2-(2'-methoxy-4'-methanesulfonylamino-phenyl)-benzimidazole, dissolved in 300 ml of absolute tetrahydrofuran, was added dropwise, under stirring, to a suspension of 700 mg of lithium aluminium hydride in 50 ml of absolute tetrahydrofuran. After the solution was stirred overnight at ambient temperature, 30 ml of water were added, any insoluble components were filtered off, and the filtrate was concentrated to dryness in vacuo. The crude product thus obtained was purified by chromatography over 200 gm of silica gel (eluant: methylene chloride with 3 to 10% of ethanol).

Workup

  1. additionwas added dropwise
  2. filtrationany insoluble components were filtered off
  3. concentrationthe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-72c89f9203114d3a85fbf9f1af9646f7
Source dataset
uspto-grants-1987_09
Patent number
US04696931

Reaction notes

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