Acetic Anhydride → 3-Acetamidopyrazine-2-carboxylic acid o-toluamide

HRID 430514Notes

Reaction equation

HRID 430514 reaction equation
[C:1]1([CH3:10])[C:2]([C:7]([NH2:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][C:12]1[C:13]([C:18]([OH:20])=[O:19])=[N:14][CH:15]=[CH:16][N:17]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:1]1([CH3:10])[C:2]([C:7]([NH2:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:21]([NH:11][C:12]1[C:13]([C:18]([OH:20])=[O:19])=[N:14][CH:15]=[CH:16][N:17]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 697096873-Aminopyrazine-2carboxylic acid o-toluamide

Product 1

HCID 697097723-Acetamidopyrazine-2-carboxylic acid o-toluamideYield 76%

Procedure

A mixture of 3-aminopyrazine-2carboxylic acid o-toluamide (1.0 g, 4.39 mmol) and acetic anhydride (12 mL) was refluxed 2 hours. The solvent was removed and the residue was triturated with hot ethyl acetate. The ethyl acetate slurry was cooled and the product was collected and rinsed with ether to afford 0.893 g (76%) of 3-acetamidopyrazine-2-carboxylic acid o-toluamide.

Workup

  1. temperaturewas refluxed 2 hours
  2. customThe solvent was removed
  3. customthe residue was triturated with hot ethyl acetate
  4. temperatureThe ethyl acetate slurry was cooled
  5. customthe product was collected
  6. washrinsed with ether

Sources & evidence

ORD record
ord-00264fb35d554e869a4f49c0ccb5dfa0
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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