Phosphorus oxychloride → HCID 58961588, compound

HRID 916951Notes

Reaction equation

HRID 916951 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:13]1[N:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:10]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)=[CH:11][C:12]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69416016HCID 69416016, compound

Product 1

HCID 58961588HCID 58961588, compound

Procedure

To a dried round bottom flask fitted with a condenser was added methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate from Step A of Example 51 (1.50 g; 3.67 mmol) and excess phosphorous oxychloride (4 mL). The reaction mixture was heated to reflux for 16 hours. The reaction mixture was allowed to cool to room temperature, and the volatiles were removed in vacuo. The residue was redissolved in methylene chloride and washed with saturated NaHCO3 solution (2×), water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-10% ethyl acetate:hexane) to afford the desired product: m/e=428 (M+2) Rt=4.42 min on LCMS.

Workup

  1. customTo a dried round bottom flask fitted with a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 16 hours
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe residue was redissolved in methylene chloride
  6. washwashed with saturated NaHCO3 solution (2×), water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification

Sources & evidence

ORD record
ord-0252fc611eaa46a59a7f390f902de812
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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