Dimethylformamide → HCID 57978005, compound

HRID 1865819Notes

Reaction equation

HRID 1865819 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[NH:4]NC(=O)[C:7]=1[Cl:8].[CH3:11][N:12]([CH:14]=[O:15])C.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCCCCC.O>[CH2:11]([N:12]1[C:14](=[O:15])[C:7]([Cl:8])=[C:2]([Cl:1])[C:3]([O:4][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:10]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2414464,5-dichloropyridazine-3,6-diol

Product 1

HCID 57978005HCID 57978005, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

To a round bottom flask was added 4,5-dichloro-1,2-dihydropyridazine-3,6-dione (20 gm, 73.8 mmol), DMF (200 ml), potassium carbonate (20.36 gm, 147.6 mmol) and benzylbromide (15.14 gm, 88.56 mmol). The reaction was stirred at 50° C. for 6 hrs and then stirred at rt overnight. After this time, the reaction was poured into a 1:1 water: hexane mixture (2000 mL). The resultant mixture was stirred at rt for 1 h. A solid precipitate formed and the precipitate was collected by filtration to give the title compound, 2-benzyl-6-(benzyloxy)-4,5-dichloropyridazin-3(2H)-one (23.9 gm, 90% yield) as light yellow solid. 1(DMSO-D6): 7.45 (m, 2H), 7.35 (m, 4H), 7.30 (m, 4H), 5.26 (s, 2H), 5.17 (s, 2H).

Workup

  1. stirringstirred at rt overnight
  2. customA solid precipitate formed
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4ce057238e3e4cd8b8988856ab745695
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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