Ammonium formate → HCID 67273003, compound

HRID 1698569Notes

Reaction equation

HRID 1698569 reaction equation
[CH2:1](/[C:3](/[C:6]1[C:14]2[NH:13][C:12](=[O:15])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH:4]\[CH3:5])[CH3:2].C(/C(/C1C2NC(=O)NC=2C=CC=1)=C/C)C.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:1]([CH:3]([C:6]1[C:14]2[NH:13][C:12](=[O:15])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 672718674-[(1Z)-1-ethylprop-1-en-1-yl]-1,3-dihydro-2H-benzimidazol-2-oneHCID 672718704-[(1E)-1-ethylprop-1-en-1-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 67273003HCID 67273003, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of a mixture of 4-[(1E)-1-ethylprop-1-en-1-yl]-1,3-dihydro-2H-benzimidazol-2-one and 4-[(1Z)-1-ethylprop-1-en-1-yl]-1,3-dihydro-2H-benzimidazol-2-one (329 mg, 1.63 mmol) and ammonium formate (820 mg, 13.0 mmol) in ethanol (3 mL) was added 10% palladium on carbon (50% wet; 120 mg), and the mixture was stirred at room temperature for 15 hours. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate (X1). The organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo to give 354 mg (>99%) of the title compound as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate (X1)
  5. washThe organic layer was washed with brine (X1)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2008cabe6cf49718e00aad7729385fa
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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