7-(1-Ethylprop-1-en-1-yl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one → 7-(1-Ethylpropyl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698605Notes

Reaction equation

HRID 1698605 reaction equation
[CH2:1]([C:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=[O:15])[NH:14][C:10]=2[C:9]([C:17]([F:20])([F:19])[F:18])=[CH:8][CH:7]=1)=[CH:4][CH3:5])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=[O:15])[NH:14][C:10]=2[C:9]([C:17]([F:18])([F:20])[F:19])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 672729457-(1-Ethylprop-1-en-1-yl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672729847-(1-Ethylpropyl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7-(1-ethylprop-1-en-1-yl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one (486 mg, 1.71 mmol), 10% palladium on carbon (200 mg) and acetic acid (5 ml) was hydrogenated under 5 atom of hydrogen at 50° C. for 2 h. Catalyst was filtered off and filtrates were concentrated in vacuo. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by recrystallization from diisopropylether/n-hexane to give 350 mg (1.22 mmol, 72%) of the title compound as a white powder.

Workup

  1. filtrationCatalyst was filtered off
  2. concentrationfiltrates were concentrated in vacuo
  3. additionAqueous saturated sodium bicarbonate was added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by recrystallization from diisopropylether/n-hexane

Sources & evidence

ORD record
ord-3210b45f15e54f20a26074f1dbf49c08
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

Loading…