Acetic Acid → HCID 68751071, compound

HRID 1912926Notes

Reaction equation

HRID 1912926 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([NH2:15])[NH:8][N:7]=1.CN(C)[CH:18]=[CH:19][CH:20]=O>CCO>[NH2:15][C:9]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:6]2[N:5]=[CH:18][CH:19]=[CH:20][N:7]2[N:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 791253-(Dimethylamino)-2-propenalHCID 3617491H-Pyrazole-4-carboxylic acid, 3,5-diamino-, methyl ester

Product 1

HCID 68751071HCID 68751071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid (0.013 mL, 0.221 mmol) was added to a mixture of methyl 3,5-diamino-1H-pyrazole-4-carboxylate (689 mg, 4.41 mmol, prepared as described in J. Prakt. Chem. 1965, 27, 239-250) and 3-dimethylaminoacrylaldehyde (531 mg, 5.36 mmol) in EtOH (9 mL), and the mixture was heated at reflux for 22 hours, and then cooled to room temperature. The slurry was concentrated under vacuum, and the residue was dissolved in hot methanol (20 mL), allowed to cool to room temperature, then filtered and dried to provide the title compound, in sufficient purity for use in the next step. MS (ESI) m/z 193 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 22 hours
  3. concentrationThe slurry was concentrated under vacuum
  4. dissolutionthe residue was dissolved in hot methanol (20 mL)
  5. temperatureto cool to room temperature
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-70e098f5625a4096ab18c8fdd6c1f19c
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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