Toluene → HCID 57977987, compound

HRID 1865821Notes

Reaction equation

HRID 1865821 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:10]([O:29]CC2C=CC=CC=2)=[N:9]1)C1C=CC=CC=1.C1(C)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:11]2[C:10](=[O:29])[NH:9][NH:8][C:13](=[O:14])[C:12]=2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 57977995HCID 57977995, compound

Product 1

HCID 57977987HCID 57977987, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 2-benzyl-6-(benzyloxy)-4,5-bis(4-chlorophenyl)pyridazin-3(2H)-one (15.5 gm, 30.21 mmol), toluene (70 ml) and aluminum chloride (10.08 gm, 75.54 mmol). The reaction was stirred at 90° C. for 2 h. After this time, the reaction was cooled to 0° C. and water (200 ml) was slowly added to the reaction. The solution was extracted with ethyl acetate (3 L). The organic layer was washed with water (200 ml) and saturated aqueous NaCl (200 ml). The organic layer was dried (MgSO4), filtered and concentrated. The title compound, 4,5-bis(4-chlorophenyl)-1,2-dihydropyridazine-3,6-dione, was obtained as a solid and used in next reaction without further purification. MS (M+H)=330.9, 333.0.

Workup

  1. temperatureAfter this time, the reaction was cooled to 0° C.
  2. extractionThe solution was extracted with ethyl acetate (3 L)
  3. washThe organic layer was washed with water (200 ml) and saturated aqueous NaCl (200 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8853d20efa6743e5ada7f64b94c889a3
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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