Phosphorus oxychloride → 3-Chloro-6-(3-methylpentan-3-yl)pyridazine

HRID 434586Notes

Reaction equation

HRID 434586 reaction equation
[CH2:1]([C:3]([C:7]1[CH:8]=[CH:9][C:10](=O)[NH:11][N:12]=1)([CH3:6])[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:10]1[N:11]=[N:12][C:7]([C:3]([CH2:4][CH3:5])([CH3:6])[CH2:1][CH3:2])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 131886886-(3-Methylpentan-3-yl)pyridazin-3(2H)-one

Product 1

HCID 131886893-Chloro-6-(3-methylpentan-3-yl)pyridazine

Procedure

To 34 g. of 6-(1-ethyl-1-methylpropyl)pyridazin-3-one was added 175 ml. of phosphorus oxychloride, and the mixture was stirred under reflux for 30 minutes. It was then cooled, excess phosphorus oxychloride was removed under vacuum, and the residual oil was poured into ice water. The residue was made basic to pH 9 with ammonia, and triturated. The aqueous mixture so prepared was extracted with two one-liter portions of diethyl ether, and the combined organics were dried and evaporated under vacuum to obtain 35 g. of the desired product, identified by mass spectroscopy, which showed a molecular ion having a weight of 198.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureIt was then cooled
  3. customexcess phosphorus oxychloride was removed under vacuum
  4. additionthe residual oil was poured into ice water
  5. customtriturated
  6. customThe aqueous mixture so prepared
  7. extractionwas extracted with two one-liter portions of diethyl ether
  8. customthe combined organics were dried
  9. customevaporated under vacuum
  10. customto obtain 35 g

Sources & evidence

ORD record
ord-ca3603cffb6a426cbefdf2bf71744a35
Source dataset
uspto-grants-1983_08
Patent number
US04398044

Reaction notes

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