Ethyl cyanoacetate → HCID 22006193, compound

HRID 1740323Notes

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

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). 1H NMR(400 MHz, CDCl3) 2.35 (s, 3 H), 2.52 (s, 3 H), 3.78 (s, 3 H), 6.82 (d, J=9.2 Hz, 2 H), 7.18 (d, J=8 Hz, 2 H), 7.34 (d, J=8 Hz, 2 H), 7.36 (d, J=9.2 Hz, 2 H).

Workup

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

Sources & evidence

ORD record: ord-3baeff7e2d5d4be8b0a0b7253ccd0dce
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05969017

Reaction notes

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