Phosphorus oxychloride → 2-Pyridone

HRID 992892노트

반응식

HRID 992892 반응식
ClC1C=CC([CH:8]2[C:13](=[O:14])[CH:12]=[C:11](C(F)(F)F)[N:10](C)[C:9]2=[O:20])=CC=1.P(Cl)(Cl)(Cl)=O>CCN(C1C=CC=CC=1)CC>[NH:10]1[CH:11]=[CH:12][CH:13]=[CH:8][C:9]1=[O:20].[N:10]1[CH:9]=[CH:8][C:13](=[O:14])[CH2:12][CH:11]=1

참가 물질

5

반응물 2

HCID 24813Phosphorus oxychlorideHCID 184083273-(4-Chlorophenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyridine

생성물 2

HCID 88712-Pyridone수율 37%HCID 17984897Piridin-4-one수율 29%

시약·촉매·용매 1

HCID 7061N,N-Diethylaniline용매

반응 조건

온도
110 °C

실험 절차

3.3 g (10.9 mmol) of 3-(4-chlorophenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyridine was added to 8.3 g (42.3 mmol) of phosphorus oxychloride and 30 ml of diethylaniline, followed by stirring at from 100 to 120° C. for 4 hours. The reaction solution was distilled off under reduced pressure, and ethyl acetate was added to the obtained residue, followed by washing with water and a saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was separated and purified by high performance liquid chromatography to obtain 1.3 g (yield: 37%) of the desired 2-pyridone compound (Compound No. 11-1) and 1.0 g (yield: 29%) of the 4-pyridone compound (Compound No. 13-1), respectively.

후처리

  1. distillationThe reaction solution was distilled off under reduced pressure, and ethyl acetate
  2. additionwas added to the obtained residue
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe organic layer was distilled off under reduced pressure
  6. customthe obtained residue was separated
  7. custompurified by high performance liquid chromatography

출처 및 근거

ORD 기록
ord-eb0bbde8f2f64e3c94eb4417c4d2b211
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472348B1

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