Dimethyl Sulfoxide → 5-(2-Chloro-6-methoxyphenyl)-1,3-oxazolidine-2,4-dione

HRID 647183Notes

Reaction equation

HRID 647183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[CH:9]1[O:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].CS(C)=O.[CH3:20][O-:21].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:21][CH3:20])[C:3]=1[CH:9]1[O:13][C:12](=[O:14])[NH:11][C:10]1=[O:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 10942334Sodium MethoxideHCID 13092017HCID 13092017, compound

Product 1

HCID 130920155-(2-Chloro-6-methoxyphenyl)-1,3-oxazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
106 °C

Procedure

5-(2-Chloro-6-fluorophenyl)oxazolidine-2,4-dione (22 g., 0.096 mole) was taken into a mixture of dimethylsulfoxide (100 ml.) and methanol (31.5 ml.). Sodium methoxide (10.8 g., 0.2 mole) was added over about 4 minutes, during which time the temperature of the reaction mixture rose to 57° C. As a matter of convenience the reaction mixture was allowed to stand for 16 hours at room temperature before heating at 106° C. for 5 hours. After cooling to 65° C., the reaction mixture was quenched by pouring into 450 ml. of ice and water, treated with activated carbon, filtered, and made strongly acidic with conc. hydrochloric acid. The precipitated product was recovered by filtration and the wet cake slurried in 100 ml. of toluene. Water was removed by azotropic distillation in vacuo. The residual slurry was taken into solution by the addition of 100 ml. acetone and warming. After clarification, the acetone was removed by evaporation in vacuo (final volume 70 ml.). Filtration gave purified 5-(2-chloro-6-methoxyoxazolidine-2,4-dione (20.3 g., m.p. 199°-202° C.). A lower melting second crop (0.9 g.) was obtained from mother liquor.

Workup

  1. customrose to 57° C
  2. temperatureAfter cooling to 65° C.
  3. customthe reaction mixture was quenched
  4. additionby pouring into 450 ml
  5. additionof ice and water, treated with activated carbon
  6. filtrationfiltered
  7. filtrationThe precipitated product was recovered by filtration
  8. customWater was removed by azotropic distillation in vacuo
  9. additionThe residual slurry was taken into solution by the addition of 100 ml
  10. temperatureacetone and warming
  11. customAfter clarification, the acetone was removed by evaporation in vacuo (final volume 70 ml
  12. filtrationFiltration
  13. customgave
  14. custompurified 5-(2-chloro-6-methoxyoxazolidine-2,4-dione (20.3 g., m.p. 199°-202° C.)
  15. customwas obtained from mother liquor

Sources & evidence

ORD record
ord-1439e2c363014a97a4215d5416f0f241
Source dataset
uspto-grants-1983_10
Patent number
US04407811

Reaction notes

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