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

HRID 424918Notes

Reaction equation

HRID 424918 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4](O)([C:20]([F:23])([F:22])[F:21])[C:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[NH:7][C:6]=1[CH3:19].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[C:4](=[C:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:7]=[C:6]1[CH3:19])[C:20]([F:23])([F:21])[F:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 441398202,5-dihydro-alpha-hydroxy-1-(3-methoxyphenyl)-3-methyl-5-oxo-alpha-trifluoromethyl-1H-pyrazole-4-acetic acid methyl ester

Product 1

HCID 667015482-[1,5-dihydro-1-(3-methoxyphenyl)-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 2,5-dihydro-α-hydroxy-1-(3-methoxyphenyl)-3-methyl-5-oxo-α-trifluoromethyl-1H-pyrazole-4-acetic acid methyl ester (180 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 (171 mg).

Workup

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

Sources & evidence

ORD record
ord-552a804f2c5a479bbf7bfedf03ad0f29
Source dataset
uspto-grants-2012_01
Patent number
US08106086B2

Reaction notes

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