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

HRID 871755노트

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HRID 871755 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 202977953-Ethyl-1-phenyl-1H-pyrazol-5-amine

생성물 1

HCID 66877385phenyl 3-ethyl-1-phenyl-1H-pyrazol-5-ylcarbamate수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-5 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-47c565aca82543d3b55fda51b92153a4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969587B2

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