Propionitrile → HCID 12026700, compound

HRID 1695222Notes

Reaction equation

HRID 1695222 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5]NN=1.COC(=O)C1C=CC(OCC2CC2)=C(Cl)C=1.[CH3:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28]C)=O.[H-].[Na+].C(#N)CC>C1(C)C=CC=CC=1.O>[CH3:5][CH:6]([C:26](=[O:28])[C:25]1[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=1[CH3:23])[C:2]#[N:1]

Participants

8

Reactant 5

HCID 7854PropionitrileHCID 24758Sodium hydrideHCID 33094Methyl o-toluateHCID 67015924HCID 67015924, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 12026700HCID 12026700, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The product was prepared according to the general procedure for aminopyrazole synthesis (route A1). The mixture of methyl 2-methylbenzoate (3.0 mL, 20.0 mmol, 1.0 eq) and NaH (1.6 g, 40.0 mmol, 2.0 eq) in dry toluene (20 mL) was heated at 80° C. and then propionitrile (6.7 mL, 94.4 mmol. 4.7 eq) was added dropwise; the reaction was heated for 18 hours. The crude product was dissolved in water and extracted with DCM, and it was used in the following step without further purification (3.04 g, yield: 88%).

Workup

  1. customThe product was prepared
  2. temperaturethe reaction was heated for 18 hours
  3. extractionextracted with DCM, and it
  4. customwas used in the following step without further purification (3.04 g, yield: 88%)

Sources & evidence

ORD record
ord-372504a95b524c67974d814a43afbba8
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

Loading…