Phosphorus oxychloride → HCID 18989574, compound

HRID 2395702Notes

Reaction equation

HRID 2395702 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](=[O:12])[CH3:11])=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:13]([C:9]1[N:8]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[O:12][C:10]=1[CH3:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54525816HCID 54525816, compound

Product 1

HCID 18989574HCID 18989574, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(1-benzyl-2-oxopropyl)malonamidic acid ethyl ester (7.0 g), phosphorus oxychloride (POCl3) (5.8 g) and toluene (40 ml) was stirred under refluxing conditions for 1 hour. The reaction mixture was concentrated under reduced pressure; the residue was then neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography. From the fraction eluted with hexane-ethyl acetate (1:3, v/v), ethyl 2-(4-benzyl-5-methyl-2-oxazolyl)acetate (4.76 g, 63%) was obtained as an oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. washFrom the fraction eluted with hexane-ethyl acetate (1:3

Sources & evidence

ORD record
ord-edf29df7bb944d2392be6be7e36754c0
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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