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2,4,6-Trimethylpyridine → 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1-[2-((3-(trifluoromethyl)phenyl)sulfonyl)ethyl]-1H-pyrazole

HRID 1016606
Notes
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Reaction equation

HRID 1016606 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[C:32]([S:36]([CH2:39][CH2:40]Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:11][N:10]([CH2:40][CH2:39][S:36]([C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([F:42])([F:28])[F:43])[CH:31]=3)(=[O:37])=[O:38])[N:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 27365062-Chloroethyl-[3-(trifluoromethyl)phenyl]sulphoneHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 116846303-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1-[2-((3-(trifluoromethyl)phenyl)sulfonyl)ethyl]-1H-pyrazoleYield 19.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Procedure

To a stirred mixture of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.7 gram, 6.60 mmol) and collidine (2 ml) in acetonitrile (25 ml) was slowly added a solution of 2-((3-(trifluoromethyl)phenyl)sulfonyl)ethyl chloride (1.5 gram, 5.50 mmol) in acetonitrile (20 ml) and the resulting solution was heated at reflux temperature for 16 hours. After concentration in vacuo the residue was dissolved in ethylacetate and washed with aqueous sodium hydrogencarbonate solution. The resulting ethylacetate layer was successively washed with 1 N hydrochloric acid solution and aqueous sodium hydrogencarbonate solution. Subsequent flash chromatographic purification (petroleum ether/diethyl ether=1/2 (v/v)) gave an oil which was crystallised from diisopropyl ether to afford 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1-[2-((3-(trifluoromethyl)phenyl)sulfonyl)ethyl]-1H-pyrazole (0.52 gram, 19% yield). Melting point: 118-119° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux temperature for 16 hours
  3. concentrationAfter concentration in vacuo the residue
  4. dissolutionwas dissolved in ethylacetate
  5. washwashed with aqueous sodium hydrogencarbonate solution
  6. washThe resulting ethylacetate layer was successively washed with 1 N hydrochloric acid solution and aqueous sodium hydrogencarbonate solution
  7. customSubsequent flash chromatographic purification (petroleum ether/diethyl ether=1/2 (v/v))
  8. customgave an oil which
  9. customwas crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-58121c53c8da428fa64edfc96f805236
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06476060B2

Reaction notes

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