Phosphorus oxychloride → HCID 20546026, compound

HRID 2059187Notes

Reaction equation

HRID 2059187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12](=O)[CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:6]=[CH:7][CH:8]=1.O=P(Cl)(Cl)[Cl:28]>C(Cl)(Cl)Cl>[ClH:28].[CH3:17][N:16]([CH3:18])[C:14]([CH:13]([C:12]1[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:9][CH2:10][N:11]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70538802HCID 70538802, compound

Product 1

HCID 20546026HCID 20546026, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

An amount of 3.9 gm (11.5 mmol) of phenylmalonic acid dimethylamide-[2-(3-methoxyphenyl)-ethylamide] was dissolved in 60 ml of chloroform, and the resulting solution was then mixed with 13.7 gm (90 mmol) of POCl3 and refluxed for 6 hours. The solvent was removed in a rotary vaporizer, the residue was dissolved in CH2Cl2, and that solution was added dropwise to a cold saturated K2CO3 solution. After extraction three times with CH2Cl2, the combined organic extracts were extracted three times with 2 N HCl. The combined HCl phases were made alkaline with K2CO3 and again extracted with CH2Cl2. The organic phase was dried and then concentrated under reduced pressure, and the residue was treated with ethereal HCl. The hydrochloride precipitated was dissolved in isopropanol, the solution was treated with active charcoal, and diethyl ether was added to the solution until the solution began to become turbid. After being left overnight in a refrigerator, the desired compound crystallized out as the hydrochloride.

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe solvent was removed in a rotary vaporizer
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. additionthat solution was added dropwise to a cold saturated K2CO3 solution
  5. extractionAfter extraction three times with CH2Cl2
  6. extractionthe combined organic extracts were extracted three times with 2 N HCl
  7. extractionagain extracted with CH2Cl2
  8. customThe organic phase was dried
  9. concentrationconcentrated under reduced pressure
  10. additionthe residue was treated with ethereal HCl
  11. customThe hydrochloride precipitated
  12. dissolutionwas dissolved in isopropanol
  13. additionthe solution was treated with active charcoal, and diethyl ether
  14. additionwas added to the solution until the solution
  15. customthe desired compound crystallized out as the hydrochloride

Sources & evidence

ORD record
ord-6b7f527bc3864dbf9bb3b3f4fc434e74
Source dataset
uspto-grants-1982_03
Patent number
US04322418

Reaction notes

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