Hydrochloric Acid → 3-tert-Butyl-1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-amine

HRID 571097Notes

Reaction equation

HRID 571097 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.[CH3:15][C:16]([CH3:23])([CH3:22])[C:17](=O)[CH2:18][C:19]#[N:20].Cl>CCO>[C:16]([C:17]1[CH:18]=[C:19]([NH2:20])[N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]([F:13])([F:14])[F:2])=[CH:10][CH:9]=2)[N:12]=1)([CH3:23])([CH3:22])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 674569593-tert-Butyl-1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-(trifluoromethoxy)phenyl)hydrazine hydrochloride (1.83 g, 8.01 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.10 g, 8.81 mmol) in a mixture of conc hydrochloric acid (12 M, 2.0 mL) and EtOH (20 mL) was heated at reflux for 18 hr. The mixture was cooled to RT and was partitioned between aq. NaOH (2.0 M, 50 mL) and ether (100 mL). The organic layer was separated and was washed with brine (100 mL) and then dried and evaporated in vacuo to afford the title compound, Intermediate A27, as a yellow solid (2.22 g, 91%); Rt 2.29 min (Method 2); m/z 300 (M+H)+, (ES+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. customwas partitioned between aq. NaOH (2.0 M, 50 mL) and ether (100 mL)
  4. customThe organic layer was separated
  5. washwas washed with brine (100 mL)
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c6ed998e7abf4de6a00916ba97481b7a
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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