Phosphorus oxychloride → 3,4,5-Trichloropyridazine

HRID 1845997Notes

Reaction equation

HRID 1845997 reaction equation
[Cl:1][C:2]1[C:3](=O)[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].O=P(Cl)(Cl)[Cl:12]>C1(C)C=CC=CC=1>[Cl:12][C:3]1[N:4]=[N:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 732474,5-Dichloro-3-hydroxypyridazine

Product 1

HCID 701113,4,5-TrichloropyridazineYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,5-dichloropyridazin-3(2H)-one (10.0 g, 60.6 mmole) in POCl3 (60 mL, 642 mmole) was stirred at 110° C. for 18 hours. Toluene was added and the solvents removed under reduced pressure. EtOAc (200 mL) and water were added to the resulting residue and the organic layer washed with water and brine and then dried over MgSO4. Concentration under reduced pressure provided the desired product as an off white solid in 90% yield, 10 g.

Workup

  1. customthe solvents removed under reduced pressure
  2. additionEtOAc (200 mL) and water were added to the resulting residue
  3. washthe organic layer washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-30713a46e62f447aa702c429a409101c
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…