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

HRID 323572Notes

Reaction equation

HRID 323572 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

A flasked 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 vacuo 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-pyridazinecarbontrile, mp 146-148° C. (EtOH).

Workup

  1. customA flasked 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 vacuo
  6. customto yield semi pure product
  7. customThe residue was recrystallized from 1900 ml of ethanol
  8. customto yield 6-[(4-chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbontrile, mp 146-148° C. (EtOH)

Sources & evidence

ORD record
ord-89a68aa9647f400dbad6e18712e9d923
Source dataset
uspto-grants-2001_04
Patent number
US06214810B1

Reaction notes

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