Hydrochloric Acid → 1-(2-chloro-phenyl)-5-(3'-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207960Notes

Reaction equation

HRID 2207960 reaction equation
[F:1][C:2]([F:25])([C:21]([F:24])([F:23])[F:22])[C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=2)=[CH:8][CH:7]=1.Cl.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][NH2:35].Cl>C(O)C>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=3)=[CH:8][CH:7]=2)[CH2:4][C:3]([C:2]([F:25])([F:1])[C:21]([F:24])([F:23])[F:22])=[N:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 1317359334,4,5,5,5-Pentafluoro-1-(3'-methylsulfanyl-biphenyl-4-yl)-pent-1-en-3-one

Product 1

HCID 1184319481-(2-chloro-phenyl)-5-(3'-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazoleYield 57.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4,4,5,5,5-Pentafluoro-1-(3′-methylsulfanyl-biphenyl-4-yl)-pent-1-en-3-one (200.0 mg, 0.54 mmol) prepared in Step 2 of Preparation 2, 2-chlorophenylhydrazine hydrochloride (115.0 mg, 0.64 mmol) and conc. hydrochloric acid (200.0 uL) were added to ethanol (5.0 mL). The reaction mixture was stirred at 100° C. for 18 hours, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with ethyl acetate three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60) to give 154.0 mg of the titled compound as a yellow liquid.

Workup

  1. customquenched with a saturated solution of sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate three times
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow liquid residue
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60)

Sources & evidence

ORD record
ord-08eaf025624f4143900d72f23d0a2f81
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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