Water → HCID 23143330, compound

HRID 732178Notes

Reaction equation

HRID 732178 reaction equation
[CH3:1][C:2]1[O:6][C:5](=O)[NH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P(Cl)(Cl)([Cl:16])=O.N1C=CC=CC=1.O>C(#N)C>[Cl:16][C:5]1[O:6][C:2]([CH3:1])=[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 123070002(3H)-Oxazolone, 5-methyl-4-phenyl-

Product 1

HCID 23143330HCID 23143330, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 5-methyl-4-phenyl-1,3-oxazol-2(3H)-one (430 mg, 2.45 mmol) in phosphorus oxychloride (2.36 g, 14.7 mmol) was added pyridine (194 mg, 2.45 mmol) and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was diluted with acetonitrile and added dropwise to water (about 30° C.). The organic materials were extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (233 mg, yield 49%) as a yellow oil.

Workup

  1. extractionThe organic materials were extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-d07c2186d94441beb2a75acc0f474251
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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