Phosphorus oxychloride → 4-(4-(Benzyloxy)phenyl)-3-butyl-6-chloropyridazine

HRID 401863Notes

Reaction equation

HRID 401863 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:19][NH:18][C:17](=O)[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:28]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([Cl:28])[N:18]=[N:19][C:20]=2[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 673731035-(4-benzyloxy-phenyl)-6-butyl-2H-pyridazin-3-one

Product 1

HCID 713030894-(4-(Benzyloxy)phenyl)-3-butyl-6-chloropyridazine

Conditions

Temperature
70 °C

Procedure

A suspension of 5-(4-benzyloxy-phenyl)-6-butyl-2H-pyridazin-3-one (5.4 g, 14.73 mmol) in POCl3 (8 mL) was stirred at 70° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and to the residue was added ice (50 g). The mixture was stirred for 1 h. This was extracted with DCM (3×50 mL), the combined organic layer was dried, filtered and concentrated under reduced pressure. The resultant residue was purified by flash silica gel column chromatography eluting with in 10% ethyl acetate in hexanes to provide 4-(4-benzyloxy-phenyl)-3-butyl-6-chloro-pyridazine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added ice (50 g)
  3. stirringThe mixture was stirred for 1 h
  4. extractionThis was extracted with DCM (3×50 mL)
  5. customthe combined organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by flash silica gel column chromatography
  9. washeluting with in 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-92fb7154cfde44589804578cf0e7f196
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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