Phosphorus oxychloride → 3-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

HRID 372730Notes

Reaction equation

HRID 372730 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12](=O)[NH:13][N:14]=2)[CH:4]=1.P(Cl)(Cl)([Cl:20])=O>>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]=[N:13][C:12]([Cl:20])=[CH:11][CH:10]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 124495416-[3-(Trifluoromethyl)phenyl]pyridazin-3-ol

Product 1

HCID 124495523-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

Procedure

A mixture of 12.6 g. of 6-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone and 200 ml. of phosphorus oxychloride is heated on a steam bath for 18 hours. The mixture is concentrated under vacuum and the residue triturated with cold water. The resulting solid is washed with water and air dried to give 13.5 g. of cream colored crystals, m.p. 131°-133° C. Recrystallization from methanol gives 6-(α,α,α-trifluoro-m-tolyl)-3-chloropyridazine as white crystals, m.p. 131°-133° C.

Workup

  1. additionA mixture of 12.6 g
  2. concentrationThe mixture is concentrated under vacuum
  3. customthe residue triturated with cold water
  4. washThe resulting solid is washed with water and air
  5. customdried
  6. customto give 13.5 g
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-de7977de5bee49989108fd2055ef3762
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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