Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 118431820, compound

HRID 2207962Notes

Reaction equation

HRID 2207962 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]=[CH:32][C:31]([NH:34][NH2:35])=[CH:30][CH:29]=1>C(O)(=O)C>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:5]([C:6]3[CH:7]=[C:8]([C:12]4[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:4][C:3]([C:2]([F:25])([F:1])[C:21]([F:24])([F:23])[F:22])=[N:35]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 131735937HCID 131735937, compound

Product 1

HCID 118431820HCID 118431820, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °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 and 4-chlorophenylhydrazine hydrochloride (106.0 mg, 0.59 mmol) were added to acetic acid (3.0 mL). The reaction mixture was stirred at 120° C. for 8 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture was washed with a saturated solution of sodium hydrogen carbonate, 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 163.0 mg of the titled compound as a yellow liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60)

Sources & evidence

ORD record
ord-18d1580a7b3b4ed29741cd0c4c8cac15
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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