Phosphorus oxychloride → 3-Butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine

HRID 1971901Notes

Reaction equation

HRID 1971901 reaction equation
[CH2:1]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[CH:7][C:8](=O)[NH:9][N:10]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:27])=O>>[CH2:1]([C:5]1[N:10]=[N:9][C:8]([Cl:27])=[CH:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 673752856-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one

Product 1

HCID 866577793-Butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine

Conditions

Temperature
90 °C

Procedure

A suspension of the pyridazin-3-one (58.4 mmol, 19.1 g) in phosphorous oxychloride (292 mmol, 26.7 mL) was heated at 90° C. for 30 min with stirring during which period the starting material was fully consumed as judged by TLC. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with saturated NaHCO3 (3×100 mL), brine (100 mL), dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified on a 330 g SiO2 cartridge eluating with 0-10% ethyl acetate in hexanes to afford 3-butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine.

Workup

  1. customwas fully consumed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe volatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with saturated NaHCO3 (3×100 mL), brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified on a 330 g SiO2 cartridge eluating with 0-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-23fe628181d54ddb95272dab9482b79d
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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