Phosphorus oxychloride → HCID 69288439, compound

HRID 986950Notes

Reaction equation

HRID 986950 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C@H:11]1[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]=[C:18]2[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69292406HCID 69292406, compound

Product 1

HCID 69288439HCID 69288439, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.0 g of (−)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-methanesulfonylbenzamide are suspended in 150 ml of toluene, treated with 4 ml of phosphorus oxychloride and heated under reflux for 5.5 h. The reaction solution is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is extracted with satd sodium hydrogencarbonate solution and water. After chromatography on silica gel using petroleum etherlethyl acetate/triethylamine in the ratio 6/3/1, the title compound is obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5.5 h
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. extractionthe mixture is extracted with satd sodium hydrogencarbonate solution and water

Sources & evidence

ORD record
ord-76b384a353944b25b6f1f9f9dcd16e87
Source dataset
uspto-grants-2003_10
Patent number
US06630483B2

Reaction notes

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