1,2-Dibromoethane → 1,3-Dihydro-1-(2-bromoethyl)-3-isopropenyl-2h-benzimidazol-2-one

HRID 1591189Notes

Reaction equation

HRID 1591189 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].[Br:14][CH2:15][CH2:16]Br.[H-].[Na+]>CN(C=O)C>[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:16][CH2:15][Br:14])[C:5]1=[O:13])([CH3:3])=[CH2:2]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 190453901,3-Dihydro-1-(2-bromoethyl)-3-isopropenyl-2h-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Isopropenylbenzimidazolone (J. Davol, J. Chem. Soc., 1960, 308) was alkylated with 1,2-dibromoethane using sodium hydride in DMF. The product was purified by chromatography and crystallization from cyclohexane to give 1-isopropenyl-3-(2-bromoethyl)benzimidazolone.

Workup

  1. customThe product was purified by chromatography and crystallization from cyclohexane

Sources & evidence

ORD record
ord-64d27d942d9f4221a111dbbcafb1ce43
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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