Phosphorus oxychloride → HCID 86657817, compound

HRID 401978Notes

Reaction equation

HRID 401978 reaction equation
[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH:20]4[CH2:22][CH2:21]4)=[N:18][NH:17][C:16](=O)[CH:15]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:16]1[N:17]=[N:18][C:19]([CH:20]2[CH2:22][CH2:21]2)=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67375717HCID 67375717, compound

Product 1

HCID 86657817HCID 86657817, compoundYield 29%

Conditions

Temperature
90 °C

Procedure

A suspension of 5-(4-cyclohexyloxy-phenyl)-6-cyclopropyl-2H-pyridazin-3-one (0.86 mmol, 0.29 g) in phosphorous oxychloride (4.30 mmol, 0.40 mL) was heated at 90° C. for 20 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 (5 mL), washed with water (2 mL), saturated NaHCO3 (2×2 mL) and dried (Na2SO4). The residue was purified on a 12 g SiO2 cartridge eluting with an ethyl acetate/hexanes gradient to afford 6-chloro-4-(4-cyclohexyloxy-phenyl)-3-cyclopropyl-pyridazine (0.082 g).

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 (5 mL)
  5. washwashed with water (2 mL), saturated NaHCO3 (2×2 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-6b36172e9f9a401c9ad8d666acad946c
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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