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Potassium Carbonate → (5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-2-nitrophenyl)thio-acetic acid, ethyl ester

HRID 1440131
Notes
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Reaction equation

HRID 1440131 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16](F)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C([O-])([O-])=O.[K+].[K+].[SH:29][CH2:30][C:31](OCC)=O.CN1CC[CH2:39][C:38]1=[O:42]>O>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:22])=[CH:14][C:15]([N+:19]([O-:21])=[O:20])=[C:16]([CH2:31][C:30]([O:42][CH2:38][CH3:39])=[S:29])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 13387N-methyl-2-pyrrolidoneHCID 152785694-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 86747520(5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-2-nitrophenyl)thio-acetic acid, ethyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
28 °C

Procedure

At 25° C., 1.5 g (4.5 mmole) 4-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, 0.69 g (5.0 mmole) K2CO3, 0.55 mL (5.0 mmole) ethyl mercaptoacetate, and 0.05 g (0.5 mmole) CuF2 were slurried in 15 mL 1-methyl-2-pyrrolidinone. The reaction mixture was stirred 28° C. for 24 hours. The mixture was cooled, diluted with 100 mL cold water, and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4, and stripped in vacuo. The residue was purified chromatographically using 10% diethyl ether and 15% methylene chloride in hexane as the eluent to give 0.86 g (43%) of (5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-2-nitrophenyl)thio-acetic acid, ethyl ester as a yellow solid, mp 79° C.

Workup

  1. customAt 25° C.
  2. temperatureThe mixture was cooled
  3. extractionextracted four times with ethyl acetate
  4. washThe ethyl acetate extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-aedd61bb4ade446eb1ff4ca1a50594f6
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05496956

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes