Potassium Carbonate → phenyl 3-ethyl-1-phenyl-1H-pyrazol-5-ylcarbamate

HRID 871755Notes

Reaction equation

[CH2:1]([C:3]1[CH:7]=[C:6]([NH2:8])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C1COCC1>[CH2:1]([C:3]1[CH:7]=[C:6]([NH:8][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: -5 °C

Procedure

To a stirred mixture of 3-ethyl-1-phenyl-1H-pyrazol-5-amine (1.00 g, 5.34 mmol) and potassium carbonate (1.48 g, 10.68 mmol) in THF (50 mL) at −5° C., was added phenyl chloroformate (1.00 g, 6.41 mmol) dropwise. After stirring for a further 30 min at −5° C., the reaction mixture it was warmed to rt and stirred for a further 15 h. The mixture was quenched with water and extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate, concentrated under reduced pressure, and dried under vacuum to afford an oil. Recrystallization from petroleum ether gave phenyl 3-ethyl-1-phenyl-1H-pyrazol-5-ylcarbamate (1.00 g, 61%) as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ 10.07 (brs, 1H), 6.74-7.59 (m, 10H), 6.30 (s, 1H), 2.60 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); LC-MS (ESI) m/z 308 (M+H)+.

Workup

temperaturethe reaction mixture it was warmed to rt
stirringstirred for a further 15 h
customThe mixture was quenched with water
extractionextracted with dichloromethane
dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customdried under vacuum
customto afford an oil
customRecrystallization from petroleum ether

Sources & evidence

ORD record: ord-47c565aca82543d3b55fda51b92153a4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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