Phosphorus oxychloride → 3-Chloro-6-(4-chlorophenyl)pyridazine

HRID 372696Notes

Reaction equation

HRID 372696 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][N:13]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([Cl:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 6890856-(4-Chlorophenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

Procedure

A 269 g. portion of 6-(p-chlorophenyl)-3(2H)-pyridazinone and 1500 ml. of phosphorus oxychloride are heated on a steam bath for 5 hours. The excess phosphorus oxychloride is removed under vacuum. The solid concentrate is diluted with ice water and the resulting solid is recovered by filtration, washed with water and dried. This product is recrystallized twice from dimethylformamide-water yielding 6-(p-chlorophenyl)-3-chloropyridazine as an off-white solid, m.p. 202°-204° C.

Workup

  1. customThe excess phosphorus oxychloride is removed under vacuum
  2. concentrationThe solid concentrate
  3. additionis diluted with ice water
  4. filtrationthe resulting solid is recovered by filtration
  5. washwashed with water
  6. customdried
  7. customThis product is recrystallized twice from dimethylformamide-water

Sources & evidence

ORD record
ord-e6eb2124b3e64fc896c1dd6e50c001cd
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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