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

HRID 1917918Notes

Reaction equation

HRID 1917918 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-e437dbd906184d7b8e9e63e11422c513
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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