Dichloromethane → 5-Pentafluoroethyl-2-p-tolyl-2H-pyrazol-3-ylamine

HRID 1993675Notes

Reaction equation

HRID 1993675 reaction equation
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])[C:3](=O)[CH2:4][C:5]#[N:6].[C:13]1([CH3:21])[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.ClCCl>C(O)C>[F:1][C:2]([F:12])([C:3]1[CH:4]=[C:5]([NH2:6])[N:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:21])=[CH:14][CH:15]=2)[N:20]=1)[C:8]([F:9])([F:11])[F:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10875(4-Methylphenyl)hydrazineHCID 156138214,4,5,5,5-Pentafluoro-3-oxopentanenitrile

Product 1

HCID 578328135-Pentafluoroethyl-2-p-tolyl-2H-pyrazol-3-ylamineYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 4,4,5,5,5-pentafluoro-3-oxo-pentanenitrile (4.0 g, 21.4 mmol) and p-tolyl-hydrazine (10 g, 64.1 mmol) in ethanol (20 mL) to 95° C. in a sealed tube apparatus for 15 hours. After cooling to room temperature, remove the solvent under reduced pressure to give a yellow solid. Distribute the solid between dichloromethane (250 mL), distilled water (150 mL) and a saturated aq. sodium bicarbonate solution (50 mL). Isolate the aqueous phase and extract with dichloromethane (100 mL). Dry the combined organic phases over sodium sulfate and concentrate to give a dark gold oil. Subject oil to silica gel chromatography eluting with ethyl acetate and hexanes to give a light brown solid (3.24 g, 52% yield). MS(ES+): m/z=292.1 [M+H].

Workup

  1. temperatureHeat
  2. customremove the solvent under reduced pressure
  3. customto give a yellow solid
  4. distillationdistilled water (150 mL)
  5. customIsolate the aqueous phase
  6. extractionextract with dichloromethane (100 mL)
  7. dry with materialDry the combined organic phases over sodium sulfate
  8. concentrationconcentrate
  9. customto give a dark gold oil
  10. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-5e0b8279c0dc480a82663bbb92026953
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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