Pyridine → Methyl 2-chloro-4-(3,4-dichlorophenyl)-5-oxazolepropionate

HRID 563095Notes

Reaction equation

HRID 563095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11](=O)[O:12][C:13]=2[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8].P(Cl)(Cl)([Cl:23])=O.N1C=CC=CC=1>O>[Cl:23][C:11]1[O:12][C:13]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 12992961Methyl 3-[4-(3,4-dichlorophenyl)-2-oxo-4-oxazolin-5-yl]propionate

Product 1

HCID 23431803Methyl 2-chloro-4-(3,4-dichlorophenyl)-5-oxazolepropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
102.5 °C

Procedure

A mixture of methyl 3-[4-(3,4-dichlorophenyl)-2-oxo-4-oxazolin-5-yl]propionate (9.0 g), phosphorus oxychloride (26.2 g) and pyridine (2.25 g) was heated to 100-105° C. and stirred for 1 hour. The reaction mixture was added dropwise to heated water (100 ml) of 30° C. and extracted with ethyl acetate (150 ml×2). The organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml), and dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and methyl 2-chloro-4-(3,4-dichlorophenyl)-5-oxazolepropionate was obtained as a yellow oil (5.00 g, 52%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. additionThe reaction mixture was added dropwise
  2. extractionextracted with ethyl acetate (150 ml×2)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-6bc19292cd8d44bf9fa775b397556072
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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