Sulfuric Acid → 5-Amino-1-propyl-1H-pyrazole-4-carboxamide
Reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH3:9])[N:5]=[CH:4][C:3]=1[C:10]#[N:11].S(=O)(=O)(O)[OH:13].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH3:9])[N:5]=[CH:4][C:3]=1[C:10]([NH2:11])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A solution of 5-amino-4-cyano-1-n-propylpyrazole (J. Med. Chem., 1968, 11, 79; 4.0 g, 0.0027 mol) in a mixture of concentrated sulphuric acid (30 ml) and water (3 ml) was heated at 90° C. for 1 hour. The cool reaction mixture was poured into ice/water (70 g) and the resulting mixture basified with solid sodium carbonate to pH 8. The aqueous solution thus obtained was extracted with ethyl acetate (5×100 ml), the combined extracts dried (Na2SO4) and the solvent removed by evaporation under vacuum to give the title compound as a pale yellow solid (4.25 g, 95%). A sample was obtained as colourless crystals, m.p. 183-185° C., by crystallisation from methanol-diethyl ether. Found: C, 50.39; H, 6.94; N, 33.21. C7H12N4O requires C, 49.99; H, 7.19; N, 33.31%.
Workup
- customThe cool reaction mixture
- customThe aqueous solution thus obtained
- extractionwas extracted with ethyl acetate (5×100 ml)
- dry with materialthe combined extracts dried (Na2SO4)
- customthe solvent removed by evaporation under vacuum
Sources & evidence
- ORD record
- ord-618abb70589c472eb885731f12699f64
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06200980B1
Reaction notes
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