Phosphorus oxychloride → HCID 86657818, compound

HRID 2168710Notes

Reaction equation

HRID 2168710 reaction equation
[CH:1]1([C:7]2[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:9][C:10](=O)[NH:11][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:10]1[N:11]=[N:12][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67373395HCID 67373395, compound

Product 1

HCID 86657818HCID 86657818, compoundYield 44.4%

Conditions

Temperature
80 °C

Procedure

A suspension of 6-cyclohexyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one (0.62 mmol, 0.22 g) in phosphorous oxychloride (6.7 mmol, 0.60 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate (25 mL), washed with water (25 mL), saturated NaHCO3 (2×10 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-cyclohexyl-4-(4-cyclohexyloxy-phenyl)-pyridazine (0.102 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with water (25 mL), saturated NaHCO3 (2×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe residue was purified on a 12 g SiO2 cartridge
  7. washeluting with an ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-ac039a76deaa40318f75cd4e9ebfc7e2
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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