Ethyl cyanoacetate → HCID 22006193, compound

HRID 323574Notes

Reaction equation

HRID 323574 reaction equation
[CH3:1][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>[CH3:1][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:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 54095431HCID 54095431, compound

Product 1

HCID 22006193HCID 22006193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

An intimate, magnetically stirred mixture of 440 mg (1.40 mmol) of 1-[(4-methylphenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone 370 μl of ethylcyanoacetate and 178 mg of ammonium acetate 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 ethanol to yield 6-[(4-methylphenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile, mp 148-149° C.(EtOH).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto yield semi-pure product
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-59922d7eea8e40d9a07d4d2c28c44496
Source dataset
uspto-grants-2001_04
Patent number
US06214810B1

Reaction notes

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