Acetic Acid → HCID 14371287, compound

HRID 476893Notes

Reaction equation

HRID 476893 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:3]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4].[C:20](O)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([N:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=[C:5]1[C:3]([N:2]([CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:4])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14371283HCID 14371283, compound

Product 1

HCID 14371287HCID 14371287, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-Methyl-N-(2-pyridyl)benzimidazole-2-carboxamide (1.5 g) prepared in Example 5 was suspended in dry pyridine (20 ml), anhydrous acetic acid (1.5 g) was added at room temperature while stirring and allowed to react overnight. Pyridine was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and dried over anhydrous Na2SO4, and the solvent was distilled off. Purification of the residue by column chromatography on silica gel gave the title compound (0.75 g).

Workup

  1. customto react overnight
  2. distillationPyridine was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. distillationthe solvent was distilled off
  7. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-d2f4ca7c86dd418ebfe6998a56f3aacd
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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