Dimethylformamide → HCID 57978004, compound

HRID 1865823Notes

Reaction equation

HRID 1865823 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([OH:8])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[F:34][C:35]([F:45])([F:44])[C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1>O>[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[C:5](=[O:8])[N:6]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([C:35]([F:34])([F:44])[F:45])=[CH:43][CH:42]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 178518924HCID 178518924, compound

Product 1

HCID 57978004HCID 57978004, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask was added 6-chloro-4,5-bis(4-chlorophenyl)pyridazin-3-ol (1.5 gm, 4.26 mmol), DMF (15 ml) and K2CO3 (1.17 gm, 8.52 mmol). The reaction was stirred at rt for 30 min. After this time, 4-trifluoromethylbenzyl bromide (1.2 gm, 5.19 mmol) was added to the reaction and the reaction was stirred at rt for an additional 8 hrs. The reaction mixture was then diluted with water (40 ml). The reaction mixture was poured into a separatory funnel and extracted with EtOAc (2×50 ml). The combined organic layers were washed with water (4×30 ml) and saturated aqueous NaCl (30 ml). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated to give product 6-chloro-4,5-bis(4-chlorophenyl)-2-(4-(trifluoromethyl)benzyl)pyridazin-3(2H)-one as off white solid (1.5 gm, 65.1% yield).

Workup

  1. stirringthe reaction was stirred at rt for an additional 8 hrs
  2. additionThe reaction mixture was poured into a separatory funnel
  3. extractionextracted with EtOAc (2×50 ml)
  4. washThe combined organic layers were washed with water (4×30 ml) and saturated aqueous NaCl (30 ml)
  5. customto remove excess water
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82f63cb33448423580fa2b372f19009e
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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