Phosphorus oxychloride → HCID 21866622, compound

HRID 857220Notes

Reaction equation

HRID 857220 reaction equation
[C:1]([CH:4]([NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:2][C:1]1[O:21][C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:13][C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 21866635HCID 21866635, compound

Product 1

HCID 21866622HCID 21866622, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 6-acetyl-6-benzoylaminohexanoate (4.35 g) was dissolved in 87 ml of toluene, and 2.9 ml of phosphorus oxychloride was added and heated to reflux for 50 minutes. The reaction solution was cooled, poured into ice-cold water, neutralized with aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate and washed with brine. The resulting solution was dried over anhydrous magnesium sulfate and concentrated to provide 3.40 g of the objective compound as yellowish oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 50 minutes
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c883929c290f4052add9775c2a72a301
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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