Pyridine → HCID 23061834, compound

HRID 350725Notes

Reaction equation

HRID 350725 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10](=O)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:22])=O.N1C=CC=CC=1.C(#N)C>O>[Cl:22][C:10]1[O:11][C:12]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 23061928HCID 23061928, compound

Product 1

HCID 23061834HCID 23061834, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-[4-(3-chlorophenyl)-2-oxo-2,3-dihydro-5-oxazolyl]propionate (3.0 g), phosphorus oxychloride (4 mL) was gradually added pyridine (0.86 mL) at room temperature and the mixture was stirred at 90° C. for 3 hrs. The reaction mixture was cooled and acetonitrile was added. The mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-chloro-4-(3-chlorophenyl)-5-oxazolyl]propionate (2.3 g, 72%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e11f5f9600b64e759d3a7b0874c3dd69
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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