Triethylamine → 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile
Reaction equation
C(O[CH:4]=[C:5]([C:10]#[N:11])[CH:6](O)C#N)C.[CH:12]([NH:15][NH2:16])([CH3:14])[CH3:13].C([N:19](CC)CC)C>C(O)C>[NH2:11][C:10]1[N:15]([CH:12]([CH3:14])[CH3:13])[N:16]=[CH:4][C:5]=1[C:6]#[N:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of ethoxymethylenemalonitrile (0.55 g, 4.5 mmol) and iso-propylhydrazine (0.50 g, 4.5 mmol) in ethanol (10 mL) in a 10-20 mL Smith process vial was treated with triethylamine (0.88 mL). The vial was capped and heated in the microwave reactor for one hour at 150° C. Following cooling of the vial, the mixture was concentrated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to provide 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile as a slowly solidifying syrup (0.72 g, >100%). MS (ES+): 151.2 (M+H)+
Workup
- customThe vial was capped
- temperatureFollowing cooling of the vial, the mixture
- concentrationwas concentrated to dryness under reduced pressure
- customThe residue was partitioned between ethyl acetate and water
- extractionThe aqueous phase was extracted with ethyl acetate
- washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-7052b498e7794d859fe77d82bbf3f783
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129371B2
Reaction notes
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