Sodium Hydroxide → HCID 54347577, compound

HRID 582004Notes

Reaction equation

HRID 582004 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:3]=1[C:21]#[N:22].[OH-:23].[Na+]>C(O)C>[NH2:1][C:2]1[N:6]([C:7]([CH3:9])([CH3:10])[CH3:8])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:3]=1[C:21]([NH2:22])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24902916HCID 24902916, compound

Product 1

HCID 54347577HCID 54347577, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-amino-1-tert-butyl-4-cyano-3-(4'-trifluoromethylphenyl)pyrazole (308 mg, 1.0 mmol) in ethanol (15 ml) was added 10M sodium hydroxide (3 ml) and the mixture heated at reflux for 72 h. On cooling, ethanol was removed under reduced pressure and water (50 ml) added. The resulting precipitate was collected by filtration, and washed with water (2×25 ml), to give the title compound (200 mg) as a colorless solid after recrystallisation from ethyl acetate m.p. 210-211°. δH (CDCl3) 1.67 (9H, s), 5.16 (2H, br s), 5.69 (2H, br s), and 7.71 (4H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 72 h
  3. temperatureOn cooling
  4. customethanol was removed under reduced pressure and water (50 ml)
  5. additionadded
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water (2×25 ml)

Sources & evidence

ORD record
ord-129de6de8d19443992c9391364f54963
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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