Hydrochloric Acid → 3-Tert-butyl-1-[4-(methylthio)phenyl]-1h-pyrazol-5-amine

HRID 657834Notes

Reaction equation

HRID 657834 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>C(O)C.C(OCC)(=O)C>[C:13]([C:14]1[CH:15]=[C:16]([NH2:17])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([S:3][CH3:2])=[CH:5][CH:6]=2)[N:11]=1)([CH3:20])([CH3:19])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27609784-(Methylthio)phenylhydrazine

Product 1

HCID 689033733-Tert-butyl-1-[4-(methylthio)phenyl]-1h-pyrazol-5-amineYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Concentrated hydrochloric acid (1 mL) was added dropwise to a mixture of 4-methylthiophenyl hydrazine (2 g, 10.5 mmol) and 4,4-dimethyl-3-oxopentane nitrile (1.44 g, 11.5 mmol) in ethanol (30 mL) and the mixture was heated under reflux for 18 hours. The cooled mixture was then diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 97:3 to afford the title compound as a yellow oil that crystallised on standing (2.59 g, 95% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. washwashed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-89885915328a463aa531123764ecf763
Source dataset
uspto-grants-2011_12
Patent number
US08076356B2

Reaction notes

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