Dimethylamine → N,N-Dimethyl-2,3-dihydro-3-oxo-5,6-diphenyl-4-pyridazinecarboxamide

HRID 463965Notes

Reaction equation

HRID 463965 reaction equation
[C:1]([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)(O)=[O:2].[CH3:23][NH:24][CH3:25]>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:25])[C:1]([C:4]1[C:5](=[O:22])[NH:6][N:7]=[C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 735030F3099-5022

Product 1

HCID 13533378N,N-Dimethyl-2,3-dihydro-3-oxo-5,6-diphenyl-4-pyridazinecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.0 grams (0.0275 mole) of the acid chloride of the product of Example 2 was reacted with excess dimethylamine in 200 mls of toluene. This solution was heated on a steam bath for 2 hours. The solution was filtered and the filtrate distilled at reduced pressure. The residual solid was filtered, washed with petroleum ether and air dried. There was isolated 5.0 grams of a solid which when recrystallized from absolute ethyl alcohol gave 2.5 grams of a white solid that melted at 278° C. The infrared spectrum showed two carbonyl bands one at 6.0μ, the other a 6.1μ. Analysis calculated for C19H17N3O2.1H2O, C, 70.4; H, 5.4; N, 12.9. Found: C, 70.1; H, 5.5; N, 12.9.

Workup

  1. temperatureThis solution was heated on a steam bath for 2 hours
  2. filtrationThe solution was filtered
  3. distillationthe filtrate distilled at reduced pressure
  4. filtrationThe residual solid was filtered
  5. washwashed with petroleum ether and air
  6. customdried

Sources & evidence

ORD record
ord-8b6839e90a63456e9b55cccb1f6c26b4
Source dataset
uspto-grants-1985_10
Patent number
US04545810

Reaction notes

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