Hydrochloric Acid → 3-tert-butyl-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-5-amine

HRID 217847

Reaction equation

HRID 217847 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19].Cl>CCO.[OH-].[Na+].CCOC(C)=O>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([S:3]([CH3:2])(=[O:5])=[O:4])=[CH:11][CH:10]=2)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27351814-(Methylsulfonyl)phenylhydrazine hydrochloride

Product 1

HCID 595888283-tert-butyl-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(methylsulfonyl)phenylhydrazine hydrochloride (1.133 g, 5.09 mmol) and 4,4-dimethyl-3-oxopentanenitrile (0.697 g, 5.57 mmol) were weighed into a 100 mL RBF. 0.2 M HCl in EtOH (42 mL) was added and the suspension was heated to reflux for 27 h, during which time all solids gradually dissolved to give a yellow solution. The solution was diluted with 1 M NaOH(aq) (˜16 mL) to pH 12-13, EtOAc (70 mL) was added and the biphasic system was vigorously stirred for 5 min. The organic layer was isolated, dried (MgSO4), filtered and concentrated to give a yellow crystalline solid. Yield: 1.42 g (95%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 27 h, during which time all solids
  3. dissolutiongradually dissolved
  4. customto give a yellow solution
  5. additionwas added
  6. customThe organic layer was isolated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a yellow crystalline solid

Sources & evidence

ORD record
ord-4e01d0d226ac4ac28dcd7f14d33611df
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Linked notes

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