Hydrochloric Acid → HCID 118432140, compound

HRID 2207964Notes

Reaction equation

HRID 2207964 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:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.Cl.[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[NH:35][NH2:36].Cl>C(O)C>[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[N:35]1[CH:5]([C:6]2[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:4][C:3]([C:2]([F:25])([F:1])[C:21]([F:24])([F:23])[F:22])=[N:36]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723905(2,4-Dichlorophenyl)hydrazine monohydrochlorideHCID 131735937HCID 131735937, compound

Product 1

HCID 118432140HCID 118432140, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4,4,5,5,5-Pentafluoro-1-(4′-methylsulfanyl-biphenyl-3-yl)-pent-1-en-3-one (200.0 mg, 0.54 mmol) prepared in Step 3 of Preparation 4, 2,4-dichlorophenylhydrazine hydrochloride (127.0 mg, 0.59 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 92.0 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-f97d52ce6962487d871709c88a36448f
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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