Benzil → 4-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl-

HRID 463963Notes

Reaction equation

HRID 463963 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH2:19][C:20]([NH:22][NH2:23])=[O:21])#[N:18]>CN(C)C=O>[C:17]([C:19]1[C:20](=[O:21])[NH:22][N:23]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)#[N:18]

Participants

4

Reactant 2

HCID 8651BenzilHCID 8820Cyanoacetic acid hydrazide

Product 1

HCID 957574-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl-Yield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzil 63.1 grams (0.3 mole) along with 30 grams (0.3 mole) of cyanoacetohydrazide in 200 mls of dimethylformamide was heated at 110° C. for five hours. The solution was cooled and the precipitant solid was filtered and washed with ethyl alcohol. The filtrate was vacuum distilled and the residual solid was washed with ethyl alcohol and filtered. There was isolated 74.5 grams, a 95% yield, of a solid which melted at 280°-281° C. Calculated for C17H11N3O, C, 74.7; H, 4.1; N, 15.4. Found: C, 74.4; H, 4.16; N, 15.2. The infrared spectra showed the nitrile at 4.5μ; the ##STR57## band for an amide at 6.0μ.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe precipitant solid was filtered
  3. washwashed with ethyl alcohol
  4. distillationdistilled
  5. washthe residual solid was washed with ethyl alcohol
  6. filtrationfiltered
  7. customThere was isolated 74.5 grams

Sources & evidence

ORD record
ord-4261da5c2daf435d8758123dbaca6b4f
Source dataset
uspto-grants-1985_10
Patent number
US04545810

Reaction notes

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