Phosphorus oxychloride → 2-(1-Methyl-1H-pyrazol-5-yl)-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole

HRID 238374노트

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HRID 238374 반응식
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:11]([C:12]([NH:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=O)=[CH:10][CH:9]=[N:8]1>C(#N)C>[CH3:6][N:7]1[C:11]([C:12]2[O:27][C:16]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[N:15][N:14]=2)=[CH:10][CH:9]=[N:8]1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 866848721-Methyl-N'-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazide

생성물 1

HCID 866848732-(1-Methyl-1H-pyrazol-5-yl)-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole수율 81.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

Phosphorus oxychloride (1.80 mL) was added to an acetonitrile (4.8 mL) suspension of 1-methyl-N′-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazide (300 mg) at a room temperature, and the obtained solution was then heated to reflux at 90° C. for 15 hours. Thereafter, the reaction solution was concentrated under a reduced pressure. A saturated sodium carbonate aqueous solution was added to the residue to convert it to a basic solution, and the resulting solution was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration, so as to obtain the title compound (230 mg) in the form of a brown solid.

후처리

  1. temperaturethe obtained solution was then heated
  2. concentrationThereafter, the reaction solution was concentrated under a reduced pressure
  3. additionA saturated sodium carbonate aqueous solution was added to the residue
  4. extractionthe resulting solution was then extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated saline
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. concentrationfollowed by vacuum concentration

출처 및 근거

ORD 기록
ord-666a2e489bbf45ba8bb39f1ebde6a3a4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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