1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-3-isopropenyl-2(3H)-benzimidazolone

HRID 266692Notes

Reaction equation

HRID 266692 reaction equation
Br[CH2:2][CH2:3][Cl:4].C(=O)([O-])[O-].[K+].[K+].[C:11]([N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15]1=[O:23])([CH3:13])=[CH2:12]>CN(C)C=O>[Cl:4][CH2:3][CH2:2][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([C:11]([CH3:13])=[CH2:12])[C:15]1=[O:23]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 107050051-(2-Chloroethyl)-3-isopropenyl-2(3H)-benzimidazolone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mmol of 1-bromo-2-chloroethane and 55 mmol of potassium carbonate are added to 50 mmol of 1-isopropenyl-2(3H)-benzimidazolone in 150 ml of dimethylformamide. The whole mixture is kept stirring for 48 hours. It is then poured into ice-cold water and extracted with dichloromethane. The organic phases are washed with water, dried and evaporated. The residue is then taken up in ether. The ether phase is washed with 2N potassium hydroxide and then with water, dried and evaporated and leads to the expected product.

Workup

  1. additionIt is then poured into ice-cold water
  2. extractionextracted with dichloromethane
  3. washThe organic phases are washed with water
  4. customdried
  5. customevaporated
  6. washThe ether phase is washed with 2N potassium hydroxide
  7. dry with materialwith water, dried
  8. customevaporated

Sources & evidence

ORD record
ord-9daaa0aec22543028ba83644f283bc2b
Source dataset
uspto-grants-1997_07
Patent number
US05652246

Reaction notes

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