Dimethyl Sulfate → 1-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

HRID 485681

반응식

HRID 485681 반응식
N1C(=O)C=[CH:3]N1.[C:7]1([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][NH:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(OC)(OC)(=O)=O>C1(C)C=CC=CC=1>[CH3:3][N:14]1[CH:15]=[CH:16][C:17](=[O:18])[N:13]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 3513171H-Pyrazol-3-olHCID 27487101-phenyl-1H-pyrazol-5-ol

생성물 1

HCID 146200001-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

The pyrazolinone prepared as described above in (a) (1.153 g, 7.2 mmol) in dry toluene (3 ml) was treated with dimethyl sulphate (8 mmol, 750 μl) and the whole refluxed under nitrogen for 5 hours. The reaction mixture was then allowed to cool and in doing so separated into two phases. The upper consisting mainly of toluene was carefully pipetted off and discarded. The remaining layer was then treated with water (1 ml), the whole warmed with stirring to 50° C. and then treated with 40% sodium hydroxide solution (1 ml) and stirred at 50° C. for a further 30 minutes. The resultant solution was subsequently extracted with three portions of benzene. The first two extracts were found to contain two products which has spectral properties consistent with 2-methyl-1-phenyl-3-pyrazolin-5-one and 2,4-dimethyl-1-phenyl-3-pyrazolin-5-one. These were separated by chromatography on silica (ethyl acetate) to give 2-methyl-1-phenyl-3-pyrazolin-5-one (95 mg). The third extracton (above) consisted solely of 2-methyl-1-phenyl-3-pyrazolin-5-one (208 mg) (Total yield, 24%). νmax (CHCl3) 1655, 1595, 1550, 1495 cm-1. δ(D6Acetone) 3.11 (3H, s, --NMe), 5.44 (1H, d, J4 Hz, C4 proton), 7.47 (5H, m, phenyl protons), 7.83 (1H, d, J4 Hz, C3 proton). Found: M+ 174.0798; C10H10N2O requires M; 174.0794.

후처리

  1. temperaturethe whole refluxed under nitrogen for 5 hours
  2. temperatureto cool
  3. customin doing so separated into two phases
  4. additionThe remaining layer was then treated with water (1 ml)
  5. temperaturethe whole warmed
  6. additiontreated with 40% sodium hydroxide solution (1 ml)
  7. stirringstirred at 50° C. for a further 30 minutes
  8. extractionThe resultant solution was subsequently extracted with three portions of benzene
  9. customThese were separated by chromatography on silica (ethyl acetate)

출처 및 근거

ORD 기록
ord-44fc1f7af76e42bb9e8884210dfb514b
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04537886

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