Benzoyl chloride → HCID 22751148, compound

HRID 2163661Notes

Reaction equation

HRID 2163661 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]([C:12]1[N:13]=[N:14][C:15]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:16][C:17]=1[CH3:18])[NH2:11].C(N(CC)CC)C>O1CCOCC1>[CH3:18][C:17]1[C:12]2[N:13]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][N:10]=2)[N:14]=[C:15]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chloride2×HCID 8471TriethylamineHCID 2161094-(6-Hydrazinyl-5-methyl-3-pyridazinyl)morpholine

Product 1

HCID 22751148HCID 22751148, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compounds wherein R is phenyl are prepared by reaction of the corresponding 3-hydrazino-4-alkyl-6-morpholinopyridazine with benzoyl chloride. For example, 3.5 grams of benzoyl chloride are added to a solution of 1.48 grams of 3-hydrazino-4-methyl-6-morpholinopyridazine and 1.8 grams of triethylamine, in 200 milliliters of dioxane and the mixture is refluxed for 3 hours. After evaporation of the solvent and washing with water, the 8-methyl-6-morpholino-3-phenyl-s-triazolo[4,3-b]pyridazine product is obtained, recrystallized from ethanol and found to melt at 271°-273° C. Compounds wherein R is phenyl can also be prepared by reacting a 3-chloro-4-loweralkyl-6-morpholinopyridazine with benzoyl hydrazide, preferably in equimolar proportions and at a temperature from the fusion point of the mixture to about 200° C. The latter reaction can be carried out without a solvent or in a solvent medium such as diethylene glycol methyl ether.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. washwashing with water

Sources & evidence

ORD record
ord-93aa0b54e837448b905567c0815259a3
Source dataset
uspto-grants-1979_01
Patent number
US04136182

Reaction notes

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