Water → 2-(N,N-dimethylcarbamyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinone

HRID 463968Notes

Reaction equation

[Na].[C:2]([C:4]1[C:5](=[O:22])[NH:6][N:7]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:3].[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26].O>CN(C)C=O>[CH3:23][N:24]([CH3:28])[C:25]([N:6]1[C:5](=[O:22])[C:4]([C:2]#[N:3])=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:7]1)=[O:26]

Participants

Conditions

Temperature: 110 °C

Procedure

5.0 grams (0.016 mole) of the sodium salt of 4-cyano-5,6-diphenyl-3-(2H)-pyridazinone was reacted with 1.83 grams (0.017 mole) of dimethylcarbamyl chloride in 50 mls of dimethylformamide. This solution was heated 110° C. for 3 hours, cooled, and poured into excess water. The precipitant solid was filtered, washed with water and air dried. This solid was taken up in chloroform, dried over sodium sulfate and the solvent distilled at reduced pressure. The residual solid was recrystallized from ethyl alcohol to give 3.0 grams of a solid which melted at 231° C. The infrared spectrum showed the methyl group at 3.5μ, the nitrile band at 4.5μ, and two carbonyl bands at 5.8 and 6.0μ.

Workup

temperaturecooled
filtrationThe precipitant solid was filtered
washwashed with water and air
customdried
dry with materialdried over sodium sulfate
distillationthe solvent distilled at reduced pressure
customThe residual solid was recrystallized from ethyl alcohol

Sources & evidence

ORD record: ord-ec4cea638d0b4397932f26e3c70cfe01
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04545810

Reaction notes

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