Acetic Anhydride → HCID 178474341, compound

HRID 38672Notes

Reaction equation

HRID 38672 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1.C([O-])(O)=O.[Na+].[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:12](=[O:14])[CH3:13])=[N:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178418806HCID 178418806, compound

Product 1

HCID 178474341HCID 178474341, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1H-pyrazol-3-amine (ALDRICH, 11.32 g, 0.136 mol) was dissolved in 100 mL of distilled water. NaHCO3 (34 g, 0.408 mol) was slowly added. Acetic anhydride (27.55 g, 0.272 mol) was then added dropwise and the resulting suspension was heated at reflux overnight. Then, the mixture was allowed to cool down to r.t. and the solid obtained was filtered off and characterized as the title compound (8.4 g, 0.067 mol, 49%). After concentration of the filtrate, a second precipitate was obtained (2.7 g, 0.021 mol, 16%), also characterized as the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm: 12.23 (br s, 1H), 10.30 (br s, 1H), 7.55 (br s, 1H), 6.45 (br s, 1H), 1.97 (s, 3H). [ES+MS] m/z 126 (MH+).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux overnight
  3. customthe solid obtained
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-2e273e05783d458eb9aeaf2f9b579303
Source dataset
uspto-grants-2013_09
Patent number
US08524750B2

Reaction notes

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