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

HRID 968191Notes

Reaction equation

HRID 968191 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][NH2:14])=[N:5][N:4]=1.C(N(CC)CC)C.[C:22](Cl)(=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCOCC1>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][N:14]=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:5]2[N:4]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22288370HCID 22288370, compound

Product 1

HCID 15025636-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-chloro-4-hydrazinophthalazine hydrochloride (10 g) in dioxan (220 ml) was added triethylamine (7.24 ml) and benzoyl chloride (6.04 ml). This mixture was heated at reflux for 8 hours under nitrogen. After cooling the reaction mixture was concentrated under vacuum and the solid obtained was collected by filtration, washed with water and diethyl ether and dried under vacuum, to yield the title compound (12.0 g). 1H NMR (250 MHz, DMSO)•7.60 (3H, m), 8.00 (1H, t, J=8.4 Hz), 8.19 (1H, t, J=8.4 Hz), 8.31 (3H, m), 8.61 (1H, d, J=6.3 Hz).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 8 hours under nitrogen
  3. temperatureAfter cooling the reaction mixture
  4. concentrationwas concentrated under vacuum
  5. customthe solid obtained
  6. filtrationwas collected by filtration
  7. washwashed with water and diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7d4b1bfd1a654a56b168a92d4c0ac474
Source dataset
uspto-grants-2005_10
Patent number
US06958334B2

Reaction notes

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