Phosphorus oxychloride → HCID 21866606, compound

HRID 890648Notes

Reaction equation

HRID 890648 reaction equation
[C:1]([CH:4]([NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)(=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Br:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][C:4]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[O:15][C:1]=2[CH3:2])[CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21866659HCID 21866659, compound

Product 1

HCID 21866606HCID 21866606, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-[2-Acetyl-2-(p-toluoylamino) ethyl]-3-bromobenzene (13.26 g) was dissolved in 260 ml of toluene, and 6.8 ml of phosphorus oxychloride was added and heated to reflux for 3 hours. The reaction solution was cooled, poured into ice-cold water and extracted with ethyl acetate. The resulting solution was washed with aqueous solution of saturated sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=4:1) to provide 10.86 g of the objective compound as yellowish crystals. M.p. 74–75° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe resulting solution was washed with aqueous solution of saturated sodium hydrogen carbonate
  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=4:1)

Sources & evidence

ORD record
ord-b3b9f6c0be184a3a9bef876827684813
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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