Benzoyl chloride → 6-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

HRID 1990778Notes

Reaction equation

HRID 1990778 reaction equation
[C:1]([Cl:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([NH:21][NH2:22])=[N:13][N:12]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[Cl:9][C:1]1[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]2=[N:13][N:12]=[C:11]([C:20]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:21]2[N:22]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27937521-Chloro-4-hydrazinophthalazine

Product 1

HCID 15025636-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazineYield 74.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

128 μl (1.1 mmol) of benzoyl chloride was added to a xylene solution (10 ml) of 194 mg (1.0 mmol) of (4-chloro-phthalazin-1-yl)-hydrazine and 182 μl (1.3 mmol) of triethylamine, and stirred overnight under reflux. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with chloroform. The organic layer was washed with saturated saline solution, dried and concentrated under reduced pressure to obtain 208 mg (yield: 74%) of 6-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine as a yellow solid.

Workup

  1. temperatureunder reflux
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated saline solution
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d343d23d5e34915aaa5227b073c0434
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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