2-Hydroxy benzimidazole → HCID 67889876, compound

HRID 2175688Notes

Reaction equation

HRID 2175688 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].[H][H].[CH3:15][O:16][C:17]1[CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27](Cl)=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>CN(C=O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[NH:3][C:2]2=[O:10])=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 119852-Hydroxy benzimidazoleHCID 24758Sodium hydrideHCID 11806394(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 67889876HCID 67889876, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1H-benzo[d]imidazol-2(3H)-one (268 mg, 2 mmol) in DMF (10 mL) at 0° C. was added 60% oily sodium hydride (88 mg, 2.2 mmol). When hydrogen evolution had ceased, a solution of (E)-3-(3,4-dimethoxyphenyl)acryloyl chloride (240 mg, 0.75 mmol) in DMF (3 mL) was added and the reaction mixture allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched by addition of 1N hydrochloric acid, and extracted with DCM. The combined organic phases were washed with brine and dried over sodium sulfate. After concentration under reduced pressure, the residue was purified by flash column (hexane-EtOAc, 25:10) to give (E)-1-(3-(3,4-dimethoxyphenyl)acryloyl)-1H-benzo[d]imidazol-2(3H)-one (240 mg, 37%). LC-MS (ES-API); rt 9.02 min; m/z calculated for C18H16N2O4 [M+H]+ 325.1, found 325.0 and 347.0 ([M+Na]+).

Workup

  1. customThe reaction was quenched by addition of 1N hydrochloric acid
  2. extractionextracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was purified by flash column (hexane-EtOAc, 25:10)

Sources & evidence

ORD record
ord-4ffe7068b8de48d0a94418700011c093
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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