Hydrochloric Acid → HCID 13092032, compound

HRID 1163942Notes

Reaction equation

HRID 1163942 reaction equation
C[C:2](C)([O-:4])C.[K+].C(=O)(OC)OC.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[CH:21]([OH:25])[C:22]([NH2:24])=[O:23].Cl>O.C(O)(C)(C)C>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[CH:21]1[O:25][C:2](=[O:4])[NH:24][C:22]1=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 13093559HCID 13093559, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13092032HCID 13092032, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (5.16 g., 0.046 mole) was dissolved in 60 ml. of tert-butanol. Dimethyl carbonate (4.14 g., 0.046 mole) and then 2-(2,6-dichlorophenyl)-2-hydroxyacetamide (5 g., 0.023 mole) were added. The suspension was heated at reflux for 2 hours and cooled to room temperature. Hydrochloric acid (46 ml. of 1 N) and then 100 ml. of water were added, and the mixture extracted with three portions of methylene chloride. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Recrystallization of the residue from toluene gave purified 5-(2,6-dichlorophenyl)oxazolidine-2,4-dione (3.15 g., 50%; m.p. 151°-153° C.), ir (KBr) 1818, 1739, 1724, 1434, 1377 cm-1.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 2 hours
  3. extractionthe mixture extracted with three portions of methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customRecrystallization of the residue from toluene
  9. customgave
  10. custompurified 5-(2,6-dichlorophenyl)oxazolidine-2,4-dione (3.15 g., 50%; m.p. 151°-153° C.), ir (KBr) 1818, 1739, 1724, 1434, 1377 cm-1

Sources & evidence

ORD record
ord-548e7de95e0e4f40b21fc81ddced25f7
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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