Ethyl cyanoacetate → 6-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile

HRID 1720249노트

반응식

HRID 1720249 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9](=[N:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.C(O[C:26](=[O:30])[CH2:27][C:28]#[N:29])C.C([O-])(=O)C.[NH4+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:10]([CH3:11])=[C:27]([C:28]#[N:29])[C:26](=[O:30])[N:14]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[N:13]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 537286961-[(4-Chlorophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone

생성물 1

HCID 99080676-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
160 °C

실험 절차

A flasked equiped with a claisen distillation head and magnetic stirring was charged with mixture of 32.6 g (0.097 mole) 1-[(4-chlorophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone, 24.8 ml of ethylcyanoacetate and 12.2 g of ammonium acetate. The mixture was heated under a nitrogen atmosphere at 160° C. for 30 min. The reaction mixture was cooled and dissolved in methylene chloride. The organic layer was washed successively with sat'd aqueous sodium bicarbonate and water. The organic layer was dried over magnesium sulfate and evaporated in vacuo to yield semi pure product. The residue was recrystallized from 1900 ml of ethanol to yield 33.05 g of 6-[(4-chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile, mp 146°-148° C. (EtOH).

후처리

  1. customA flasked equiped with a claisen distillation head
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed successively with sat'd aqueous sodium bicarbonate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto yield semi pure product
  7. customThe residue was recrystallized from 1900 ml of ethanol

출처 및 근거

ORD 기록
ord-4882bb4928ff421d9eaccb5f76e418a5
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506228

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