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

HRID 323564ノート

反応式

HRID 323564 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

A flask equipped with a claisen distillation head and magnetic stirring was charged with an intimate 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 saturated aqueous sodium bicarbonate and water. The organic layer was dried over magnesium sulfate and evaporated in vacuao to yield semi pure product. The residue was recrystallized from 1900 ml of ethanol to yield 6-[(4-chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile, mp 146-148° C. (EtOH).

後処理

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

出典と根拠

ORDレコード
ord-39da0a54ee724fc8a310af3d02bf6e34
出典データセット
uspto-grants-2001_04
特許番号
US06214809B1

反応ノート

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