HCID 58011039, compound → 3-[5-Amino-3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]benzonitrile

HRID 1696425Notes

Reaction equation

HRID 1696425 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH2:12])=O)[N:5]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1>O=S(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]#[N:12])[N:5]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1

Participants

3

Reactant 1

HCID 58011039HCID 58011039, compound

Product 1

HCID 435430033-[5-Amino-3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]benzonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)benzamide (5.2 g, 20 mmol) in SOCl2 (50 mL) was heated at reflux for 6 h. After removal of the solvent, the residue was dissolved in EtOAc (100 mL). The organic layer was washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and purified by column chromatography to afford 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)benzonitrile (3.5 g, 73% yield).

Workup

  1. temperatureat reflux for 6 h
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in EtOAc (100 mL)
  4. washThe organic layer was washed with saturated NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-6d00e7b6afe447f98b3eb79682f1b644
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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