Water → 3(2H)-Pyridazinone, 4-chloro-2-(4-chlorophenyl)-5-((4-chlorophenyl)methoxy)-

HRID 1165426Notes

Reaction equation

HRID 1165426 reaction equation
[Cl:1][C:2]1[C:3](=[O:16])[N:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:5]=[CH:6][C:7]=1[OH:8].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:3](=[O:16])[N:4]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:5]=[CH:6][C:7]=1[O:8][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 546974414-Chloro-2-(4-chlorophenyl)-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 30652303(2H)-Pyridazinone, 4-chloro-2-(4-chlorophenyl)-5-((4-chlorophenyl)methoxy)-Yield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 70 ml of N,N-dimethylformamide was dissolved 7.1 g (0.028 mol) of 4-chloro-2-(4-chlorophenyl)-5-hydroxy-3(2H)-pyridazinone, and thereto were added 4.5 g of p-chlorobenzyl chloride and 5.4 g of anhydrous potassium carbonate. The resulting reaction mixture was heated under stirring on an oil bath at 120° to 130° C. for 2 hours. After allowing to cool, the reaction mixture was poured into 500 ml of water. The solid thus precipitated was taken out by filtration, washed with water, dried and then recrystallized from an ethyl acetate-benzene mixture to give 6.3 g of the intended compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto cool
  4. customThe solid thus precipitated
  5. filtrationwas taken out by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from an ethyl acetate-benzene mixture

Sources & evidence

ORD record
ord-d6219f38236f43bf825b5b80f8353636
Source dataset
uspto-grants-1990_03
Patent number
US04910201

Reaction notes

Loading…