Water → 1-(4-Cyanophenyl)-5-[4-(methylthio)phenyl]-3-(trifluoromethyl)pyrazole

HRID 1078641

Reaction equation

HRID 1078641 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=1.Cl.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1)#[N:20].O>C(O)(=O)C.CN(C)C=O>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][C:11]([C:12]([F:15])([F:14])[F:13])=[N:28]2)=[CH:23][CH:22]=1)#[N:20]

Participants

6

Reactant 3

HCID 962WaterHCID 107301701,3-Butanedione, 4,4,4-trifluoro-1-[4-(methylthio)phenyl]-HCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 229096971-(4-Cyanophenyl)-5-[4-(methylthio)phenyl]-3-(trifluoromethyl)pyrazoleYield 101.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-[4-(methylthio)phenyl]-4,4,4-trifluorobutane-1,3-dione (1.8 g) and 4-cyanophenylhydrazine hydrochloride (1.2 g) in acetic acid (30 ml) and N,N-dimethylformamide (1 ml) was stirred at 110° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated to give a brown powder of 1-(4-cyanophenyl)-5-[4-(methylthio)phenyl]-3-(trifluoromethyl)pyrazole (2.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a2dd2b517c4f4f35b1a29dbc7943f319
Source dataset
uspto-grants-1996_08
Patent number
US05550147

Linked notes

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