Acetonitrile → Pentoxazone

HRID 275104Notes

Reaction equation

HRID 275104 reaction equation
[C:1](#N)[CH3:2].[F:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([OH:12])=[CH:7][C:6]=1[N:13]1[C:17](=[O:18])[CH2:16][O:15][C:14]1=[O:19].C1(C)C=CC(S(O[CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)(=O)=O)=CC=1.[C:36](=O)([O-])[O-].[K+].[K+]>O>[F:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:7][C:6]=1[N:13]1[C:17](=[O:18])[C:16](=[C:1]([CH3:2])[CH3:36])[O:15][C:14]1=[O:19]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateHCID 20090579(2-Fluoro-4-chloro-5-hydroxyphenyl)-1,3-oxazolidine-2,4-dione

Product 1

HCID 11714234PentoxazoneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An acetonitrile solution (100 ml) containing 3N-(2-fluoro-4-chloro-5-hydroxyphenyl)-1,3-oxazolidine-2,4-dione (1.0 g, 3.50 mmol), cyclopentyl p-toluenesulfonate (1.0 g, 4.16 mmol) and potassium carbonate (0.5 g, 3.62 mmol) was heated for 4 hours under reflux. After reaction, the mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×3). The organic layer was washed with saturated sodium hydrogencarbonate aqueous solution (50 ml) and saturated brine (50 ml) and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, the solvent was removed by distillation, and 3N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione was obtained. This was purified by silica gel chromatography (ethyl acetate/hexane=1/2) to obtain a white solid of the intended product (0.99 g, 2.80 mmol). Yield: 80.0%. Spectral and other data of the product are those as shown in Example 27.

Workup

  1. temperaturewas heated for 4 hours
  2. temperatureunder reflux
  3. customAfter reaction
  4. extractionextracted with ethyl acetate (50 ml×3)
  5. washThe organic layer was washed with saturated sodium hydrogencarbonate aqueous solution (50 ml) and saturated brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-bdc434111cba4034a196f2ba2f19cc41
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

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