Water → methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

HRID 1698590Notes

Reaction equation

HRID 1698590 reaction equation
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=[O:15])[NH:14][C:10]=2C(C#N)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[OH-].[K+].O.[C:22]([O:28]C)([O:26][CH3:27])(OC)[CH3:23]>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=[O:15])[NH:14][C:10]=2[C:23]([C:22]([O:26][CH3:27])=[O:28])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 15050Trimethyl orthoacetateHCID 672726697-(1-Ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbonitrile

Product 1

HCID 67271829methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbonitrile (1.50 g, 6.17 mmol), potassium hydroxide (20.0 g, 356 mmol), water (30 ml) and ethanol (30 ml) was heated under reflux for 48 h. The reaction mixture was concentrated in vacuo. The residue was diluted with ethyl acetate and 2N hydrochloric acid was added and extracted. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to give crude carboxylic acid. Trimethyl orthoacetate (10 ml) and toluene (10 ml) were added to the residue and heated at 100° C. for 6 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 35% ethyl acetate/n-hexane to give 1.31 g (4.74 mmol, 77%) of the title compound as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate and 2N hydrochloric acid
  5. additionwas added
  6. extractionextracted
  7. washThe extracts were washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give crude carboxylic acid
  11. concentrationThe reaction mixture was concentrated in vacuo
  12. customThe residue was purified by column chromatography on silica gel with a 35% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9675903d88ca445491ef011309043e76
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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