Ethyl Acetate → N,4-dimethyl-1H-benzo[d]imidazole-2-carboxamide

HRID 429617Notes

Reaction equation

HRID 429617 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH3:10][NH:11][C:12](=[O:18])[C:13](OCC)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:9][C:3]1[C:2]2[N:1]=[C:13]([C:12](=[O:18])[NH:11][CH3:10])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 175932,3-DiaminotolueneHCID 516892Sodium BicarbonateHCID 3413434Ethyl 2-(methylamino)-2-oxoacetate

Product 1

HCID 18355052N,4-dimethyl-1H-benzo[d]imidazole-2-carboxamideYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 2,3-diaminotoluene (2.0 g) and ethyl N-methyloxamate (2.36 g) in N,N-dimethylformamide (10 ml) was stirred at 175° C. for 8 hours. After being cooled to ambient temperature, the mixture as poured into a mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate and the organic layer was separated. The organic layer was washed with brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixtue of chloroform and methanol (50:1) to give 4-methyl-2-(N-methylcarbamoyl)-1H-benzimidazole (1.17 g) as a powder.

Workup

  1. temperatureAfter being cooled to ambient temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialthe solution was dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with a mixtue of chloroform and methanol (50:1)

Sources & evidence

ORD record
ord-b19c59616ed445bab2666d558014c110
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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