Potassium Carbonate → phenyl 3-(perfluoroethyl)-1-phenyl-1H-pyrazol-5-ylcarbamate

HRID 871684Notes

Reaction equation

HRID 871684 reaction equation
[F:1][C:2]([F:19])([C:7]1[CH:11]=[C:10]([NH2:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1)[C:3]([F:6])([F:5])[F:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>C1COCC1>[F:19][C:2]([F:1])([C:7]1[CH:11]=[C:10]([NH:12][C:27](=[O:28])[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:8]=1)[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 866535313-(perfluoroethyl)-1-phenyl-1H-pyrazol-5-amine

Product 1

HCID 86653532phenyl 3-(perfluoroethyl)-1-phenyl-1H-pyrazol-5-ylcarbamateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 3-(perfluoroethyl)-1-phenyl-1H-pyrazol-5-amine (300 mg, 1.08 mmol) and potassium carbonate (223 mg, 1.62 mmol) in THF (3 mL) at rt, was added a solution of phenyl chloroformate (169 mg, 1.08 mmol) in THF (2 mL) dropwise. After stirring for a further 15 h at rt, the reaction mixture was filtered and the filtrate concentrated under reduced pressure to give an oil. Purification via silica gel flash column chromatography (eluting with a gradient of 100% petroleum ether to 5% ethyl acetate in petroleum ether) afforded phenyl 3-(perfluoroethyl)-1-phenyl-1H-pyrazol-5-ylcarbamate (360 mg, 84%) as a solid. 1H NMR (400 MHz, CDCl3) δ 7.55-7.62 (m, 5H), 7.39-7.43 (m, 2H), 7.29 (m, 1H), 7.14 (m, 2H), 6.91 (m, 1H); LC-MS (ESI) m/z 398 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give an oil
  4. customPurification via silica gel flash column chromatography (
  5. washeluting with a gradient of 100% petroleum ether to 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5377261259b34815813ee0b329a57c24
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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