Thionyl Chloride → 2-[1-(4-chlorophenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]-3,3,3-trifluoro-propanoic acid methyl ester

HRID 424915Notes

Reaction equation

HRID 424915 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4](O)([C:19]([F:22])([F:21])[F:20])[C:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:7][C:6]=1[CH3:18].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[C:4](=[C:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:7]=[C:6]1[CH3:18])[C:19]([F:21])([F:20])[F:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 441398191-(4-chlorophenyl)-2,5-dihydro-alpha-hydroxy-3-methyl-5-oxo-alpha-trifluoromethyl-1H-pyrazole-4-acetic acid methyl ester

Product 1

HCID 667016252-[1-(4-chlorophenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]-3,3,3-trifluoro-propanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene solution (5 ml) of 1-(4-chlorophenyl)-2,5-dihydro-α-hydroxy-3-methyl-5-oxo-α-trifluoromethyl-1H-pyrazole-4-acetic acid methyl ester (182 mg, 0.5 mmol), thionyl chloride (0.365 ml, 5.0 mmol) was added and the mixture was stirred under reflux for 3 hours. After concentrating the liquid reaction mixture under reduced pressure, the title compound was obtained as a reddish brown solid (173 mg).

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationAfter concentrating
  3. customthe liquid reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-79e5bdfac68a4b80b1209e82c8f665df
Source dataset
uspto-grants-2012_01
Patent number
US08106086B2

Reaction notes

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