Phosphorus oxychloride → HCID 21866606, compound

HRID 857223Notes

Reaction equation

HRID 857223 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-f8e76bc404264319b44e6cccf9b9f8d5
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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