2-(Trifluoromethyl)phenylhydrazine → 5-trifluoromethyl-2-(2-trifluoromethylphenyl)-2H-pyrazol-3-ylamine

HRID 1673008Notes

Reaction equation

HRID 1673008 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[F:13][C:14]([F:21])([F:20])[C:15](=O)[CH2:16][C:17]#[N:18]>C1(C)C=CC=CC=1>[F:13][C:14]([F:21])([F:20])[C:15]1[CH:16]=[C:17]([NH2:18])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:11])([F:12])[F:1])[N:10]=1

Participants

4

Reactant 2

HCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 592402835-trifluoromethyl-2-(2-trifluoromethylphenyl)-2H-pyrazol-3-ylamineYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-trifluoromethyl-phenylhydrazine (1.1 g, 6.3 mmol) and 4,4,4-trifluoro-3-oxobutyronitrile (0.82 g, 6.0 mmol) in toluene (3 mL, anhyd.) was heated at reflux. After 5 h the reaction mixture was allowed to cool, concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 25:75) to yield the title compound (1.1 g, 61%) as an amber liquid. 1H-NMR (CD2Cl2): δ 8.40 (1H, br s), 7.77 (1H, d), 7.59 (2H, m), 7.17 (1H, m), 3.56 (2H, s); Rf 0.45 (20% EtOAc/Hex).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. concentrationconcentrated
  4. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 25:75)

Sources & evidence

ORD record
ord-5cf2690fe2b343f0b601741a742c1597
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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