Phosphorus oxychloride → HCID 21866749, compound

HRID 890662Notes

Reaction equation

HRID 890662 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[O:13])[C:7](=O)[CH2:8][CH3:9].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[O:13][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21866700HCID 21866700, compound

Product 1

HCID 21866749HCID 21866749, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 150 ml of toluene, 6.5 g of 8-chloro-4-(p-toluoylamino)-3-octanone was dissolved, and 4.1 ml of phosphorus oxychloride was added and heated to reflux for 1.5 hours. The reaction solution was cooled, poured into ice-cold water and extracted with ethyl acetate. The extract was washed with an aqueous solution of saturated sodium hydrogen carbonate and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=8:1) to provide 5.5 g of the objective compound as yellowish crystals.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with an aqueous solution of saturated sodium hydrogen carbonate and brine sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-5141ba20bab444b9bc07d4c0b335ba3a
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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