Phosphorus oxychloride → HCID 86657819, compound

HRID 1971995Notes

Reaction equation

HRID 1971995 reaction equation
[CH:1]1([C:5]2[C:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:14][CH:13]=3)=[CH:7][C:8](=O)[NH:9][N:10]=2)[CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:8]1[N:9]=[N:10][C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67372426HCID 67372426, compound

Product 1

HCID 86657819HCID 86657819, compoundYield 59.1%

Conditions

Temperature
80 °C

Procedure

A suspension of 6-cyclobutyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one (0.74 mmol, 0.24 g) in phosphorous oxychloride (7.41 mmol, 0.68 mL) was heated at 80° C. for 20 minutes. The reaction mixture was cooled to room temperature and the volatiles were removed under reduced pressure. The residue was partitioned between ethyl acetate (5 mL) and saturated NaHCO3. The layers were separated and the organic layer was washed with saturated NaHCO3 (5 mL), brine (5 mL) and dried (Na2SO4). The residue was purified on a 12 g SiO2 cartridge eluting with an ethyl acetate/hexanes gradient to give 6-chloro-3-cyclobutyl-4-(4-cyclohexyloxy-phenyl)-pyridazine (0.15 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (5 mL) and saturated NaHCO3
  4. customThe layers were separated
  5. washthe organic layer was washed with saturated NaHCO3 (5 mL), brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe residue was purified on a 12 g SiO2 cartridge
  8. washeluting with an ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-c10f86ab53f746ed8f4a3eb3bf8934ac
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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