Sodium hydride → 1-(4-Nitrobenzyl)-2-hydroxymethylbenzimidazole

HRID 1638558Notes

Reaction equation

HRID 1638558 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[H-].[Na+].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15]>CN(C=O)C.C(OCC)(=O)C>[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:7]2[C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=[C:3]2[CH2:2][OH:1])=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 785692-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 147224751-(4-Nitrobenzyl)-2-hydroxymethylbenzimidazoleYield 62.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3 g of 2-hydroxymethylbenzimidazole in 20 mL of dried DMF at 0° was added portionwise 1 g of NaH (50% oil dispersion). After stirring at room temperature for 15 minutes, 4.3 g of p-nitrobenzyl bromide was added. The reaction mixture was stirred for 16 hours and then diluted with ethyl acetate and washed with water. The organic layers were dried and evaporated. Recrystallization from acetonitrile afforded 3.5 g of a brownish solid; m.p. 162.5-165°.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours
  2. washwashed with water
  3. customThe organic layers were dried
  4. customevaporated
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-5c4aeaeab49c43279d8cf81b4a172da3
Source dataset
uspto-grants-1989_11
Patent number
US04880804

Reaction notes

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