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

HRID 1917927Notes

Reaction equation

HRID 1917927 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([NH2:11])=[N:3]1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][N:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[CH:5][C:4]([NH:11][C:13](=[O:14])[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 229127981-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

Product 1

HCID 59394502phenyl 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-ylcarbamateYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 161C, 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine (0.38 g, 2.3 mmol) and phenyl chloroformate (0.438 g, 2.8 mmol) were reacted in the presence of K2CO3 (0.415 g, 3 mmol) in THF (10 mL), to afford phenyl 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-ylcarbamate as solid (0.465 g, 71%). 1H NMR (300 MHz, CDCl3) δ 8.05 (s, 1H), 7.17-7.45 (m, 5H), 6.93 (s, 1H), 3.91 (s, 3H); LC-MS (ESI) m/z 286 (M+H)+.

Sources & evidence

ORD record
ord-ee867eca21a34011ba39f4c6882d7c6e
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

Loading…