Hydrochloric Acid → 5-Bromo-1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one

HRID 2096794Notes

Reaction equation

HRID 2096794 reaction equation
IC.[Br:3][C:4]1[CH:13]=[CH:12]C2N[C:9](=O)[NH:10][C:6]=2[CH:5]=1.CC(C)([O-])C.[K+].Cl.C[C:22]([N:24]([CH3:26])[CH3:25])=[O:23]>>[Br:3][C:4]1[CH:13]=[CH:12][C:25]2[N:24]([CH3:26])[C:22](=[O:23])[N:10]([CH3:9])[C:6]=2[CH:5]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 31374DimethylacetamideHCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 470034475-Bromo-1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one

Procedure

Iodomethane (2.41 g) was added to a suspension of 5-bromo-1,3-dihydro-benzoimidazol-2-one (1.65 g) and potassium tert-butoxide (1.91 g) in DMA (20 ml). The mixture was stirred overnight at room temperature. The mixture was poured to 2.5N aqueous HCl (80 ml) and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. Heptane (50 ml) was added to the residue and the mixture was filtered. The residue was washed with diethyl ether and dried in vacuo to give the title compound (1.1 g) as a light brown solid. MS (m/e)=241.1 [M+H+].

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. additionHeptane (50 ml) was added to the residue
  5. filtrationthe mixture was filtered
  6. washThe residue was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c5eb8a56435d4d61b52a5e44af5b9035
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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