1,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one → 1-(Propan-2-yl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 896298Notes

Reaction equation

HRID 896298 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]>[Pd].CO>[CH: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])[CH3:2]

Participants

4

Reactant 1

HCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 16535801-(Propan-2-yl)-1,3-dihydro-2H-benzimidazol-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-isopropenyl-1,3-dihydro-benzoimidazol-2-one (J. Davoll, J. Chem. Soc. 1960, 308) (6.90 g, 39.6 mmol) and 10% palladium on carbon (1.0 g) in MeOH (50 mL) was placed in a Parr shaker under hydrogen (40 psi) for 2 h. The reaction mixture was filtered through celite and evaporated to give 6.97 g (100%) of 1-isopropyl-1,3-dihydro-benzoimidazol-2-one as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-58b3d3b3562949bbbb1f5ccef1aac301
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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