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

HRID 47938Notes

Reaction equation

HRID 47938 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 h. The reaction mixture was added dropwise to warm water (100 mL, 30° C.) and extracted with ethyl acetate (150 mL×2). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous magnesium sulfate. The organic layer was concentrated and the residue was subjected to silica gel column chromatography. The title compound was obtained as a yellow oil (5.00 g, 52%) from an eluate from ethyl acetate-hexane (1:4, v/v).

Workup

  1. additionThe reaction mixture was added dropwise
  2. extractionextracted with ethyl acetate (150 mL×2)
  3. washThe organic layer was washed with saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-68469ff3264348c8a61304bcd3ea6ca2
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Reaction notes

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