Potassium Carbonate → Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylate

HRID 1631936Notes

Reaction equation

HRID 1631936 reaction equation
[O:1]=[C:2]1[N:6](C(OCC)=O)[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].OC1NC2C=CC=CC=2N=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:1]=[C:2]1[N:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[NH:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10107575diethyl 2-oxo-1H-1,3-benzimidazole-1,3(2H)-dicarboxylateHCID 178517141HCID 178517141, compound

Product 1

HCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 11.0 g (39.5 mmol) of diethyl 2-oxobenzimidazole-1,3-dicarboxylate (III), 5.30 g (39.5 mmol) of 2-hydroxybenzimidazole and 6.55 g (47.4 mmol) of potassium carbonate in acetonitrile (200 ml) was heated under reflux with vigorous stirring for 2 h. Most of the solvent was then removed in vacuo, and the residue was mixed with 150 ml of 1N hydrochloric acid. The solid residue was filtered, washed with water, dried in vacuo and recrystallized from toluene.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customMost of the solvent was then removed in vacuo
  4. additionthe residue was mixed with 150 ml of 1N hydrochloric acid
  5. filtrationThe solid residue was filtered
  6. washwashed with water
  7. customdried in vacuo
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e08e848897be488d8ced6227070b7aad
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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