Hydrochloric Acid → Methyl 3-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

HRID 725142Notes

Reaction equation

HRID 725142 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:26]([NH:27][C:28]([O:30]C)=O)=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)#[N:2].C[O-].[Na+].Cl>CO>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:17]3[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=[CH:25][C:26]=3[NH:27][C:28]2=[O:30])=[CH:11][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 15654690HCID 15654690, compound

Product 1

HCID 15654691Methyl 3-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylateYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[(2'-cyanobiphenyl-4-yl)methylamino]-3-methoxycarbonylaminobenzoate (10.5 g) in methanol (100 ml) was added NaOMe (10 g), and the mixture was heated under reflux for 20 hours. The reaction mixture was neutralized with 1N-HCl and concentrated to dryness. The residue was extracted with chloroform-water. The organic layer was washed with water, dried and evaporated to dryness. The resulting crystals were recrystallized from chloroform-methanol to afford colorless needles (8.67 g, 89%), m.p. 250°-253° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. concentrationconcentrated to dryness
  4. extractionThe residue was extracted with chloroform-water
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe resulting crystals were recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-9cdbe0f0a6bf4f93a0496bffdb3132db
Source dataset
uspto-grants-1998_01
Patent number
US05705517

Reaction notes

Loading…