Water → 4-chloro-2-(4-chlorophenyl)-5-(2,4-dichlorobenzyloxy)-3(2H)-pyridazinone

HRID 1165435Notes

Reaction equation

HRID 1165435 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]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20]Cl.C(N(CC)CC)C.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][CH2:20][C:19]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:18]=1[Cl:17]

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 8471TriethylamineHCID 546974414-Chloro-2-(4-chlorophenyl)-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 140722464-chloro-2-(4-chlorophenyl)-5-(2,4-dichlorobenzyloxy)-3(2H)-pyridazinoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 50 ml of N,N-dimethylformamide were dissolved 1.5 g (5.9 m mol) of 4-chloro-2-(4-chlorophenyl)-5-hydroxy-3(2H)-pyridazinone and 1.3 g (6.6 m mol) of 2,4-dichlorobenzyl chloride, and thereto was added 0.7 g of triethylamine. The reaction mixture was heated under stirring on an oil bath at 100° to 120° C. for 7 hours. After allowing to cool, the reaction mixture was poured into 200 ml of water and the precipitated solid was taken out by filtration, washed with water, dried and then recrystallized from benzene to give 1.7 g of the intended compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto cool
  3. filtrationthe precipitated solid was taken out by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-11726e65d5724958bfad5df91ff0ff55
Source dataset
uspto-grants-1990_03
Patent number
US04910201

Reaction notes

Loading…