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

HRID 1917941Notes

Reaction equation

HRID 1917941 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([NH2:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:1]1([N:7]2[C:11]([C:12]([F:15])([F:13])[F:14])=[CH:10][C:9]([NH:16][C:18](=[O:19])[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 534033781-Phenyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

Product 1

HCID 66898801phenyl 1-phenyl-5-(trifluoromethyl)-1H-pyrazol-3-ylcarbamateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 161C, 1-phenyl-5-(trifluoromethyl)-1H-pyrazol-3-amine (0.665 g, 2.9 mmol) and phenyl chloroformate (0.548 g, 3.5 mmol) were reacted in the presence of K2CO3 (0.691 g, 5 mmol) in THF (20 mL) and purified by silica gel chromatography with 10-20% EtOAc/hexane as eluants to afford phenyl 1-phenyl-5-(trifluoromethyl)-1H-pyrazol-3-ylcarbamate as a solid (0.794 g, 79%). 1H NMR (300 MHz, CDCl3) δ 7.97 (br, 1H), 7.38-7.46 (m, 7H), 7.14-7.29 (m, 4H); LC-MS (ESI) m/z 348 (M+H)+.

Workup

  1. custompurified by silica gel chromatography with 10-20% EtOAc/hexane as eluants

Sources & evidence

ORD record
ord-c97beb286d094e89bcee190f7a5930a0
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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