Water → 1-(1H-Benzo[d]imidazol-4-yl)ethanone

HRID 1909006Notes

Reaction equation

CON(C)[C:4]([C:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5].[Li][CH3:17].[NH4+].[Cl-].O>C1COCC1>[NH:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:4](=[O:5])[CH3:17])[C:14]=2[N:13]=[CH:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 1H-benzoimidazole-4-carboxylic acid methoxy-methyl-amide (742 mg, 3.62 mmol) in THF (36 mL) at −78° C. was added MeLi (1.6M; 2.49 mL, 3.98 mmol) dropwise. The mixture was stirred at −78° C. for 2 hours before an additional 1.0 mol. eq. MeLi (2.3 mL) was added dropwise. The mixture was stirred at −78° C. for a further 2 hours before saturated aqueous NH4Cl solution was added and the mixture warmed to room temperature. Enough water was added to dissolve all solids and the phases were separated. The aqueous phase was extracted into CHCl3 (×3), dried and concentrated in vacuo to give a white solid. Trituration with EtOAc (5 mL) followed by collection by filtration and washing with 4:1 Et2O/EtOAc (5 mL) provided 1-(1H-benzoimidazol-4-yl)-ethanone (487 mg).

Workup

additionwas added
temperaturethe mixture warmed to room temperature
dissolutionto dissolve all solids
customthe phases were separated
extractionThe aqueous phase was extracted into CHCl3 (×3)
customdried
concentrationconcentrated in vacuo
customto give a white solid
filtrationTrituration with EtOAc (5 mL) followed by collection by filtration
washwashing with 4:1 Et2O/EtOAc (5 mL)

Sources & evidence

ORD record: ord-28fa676edd9844aca0affd7cf6b86003
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598217B2

Reaction notes

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