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

HRID 871517Notes

Reaction equation

HRID 871517 reaction equation
[C:1]1([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C1COCC1>[C:1]1([N:7]2[C:11]([NH:12][C:24](=[O:25])[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:10][C:9]([C:13]([F:15])([F:16])[F:14])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 431589511-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-amine

Product 1

HCID 66876880phenyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (1.136 g, 5 mmol) and K2CO3 (1.035 g, 7.5 mmol) in THF (20 mL) was dropped a solution of phenyl chloroformate (0.939 g, 6 mmol) in THF (10 mL). After stirred at room temperature overnight, the mixture was quenched with water and extracted with CH2Cl2. Extracts were dried over MgSO4, concentrated under reduced pressure, and dried under vacuum to afford phenyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate as solid (1.714 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.55 (m, 5H), 7.39 (m, 2H), 7.28 (m, 2H), 7.14 (m, 2H), 6.86 (m, 1H); LC-MS (ESI) m/z 348 (M+H)+.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialExtracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customdried under vacuum

Sources & evidence

ORD record
ord-dac6451506754ad886c51c909372c16c
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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