Dimethyl Carbonate → HCID 13092017, compound

HRID 434836Notes

Reaction equation

HRID 434836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([OH:13])[C:10]([NH2:12])=[O:11].[C:14](=O)(OC)[O:15]C.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[O:13][C:14](=[O:15])[NH:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 13093558HCID 13093558, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13092017HCID 13092017, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-(2-Chloro-6-fluorophenyl)-2-hydroxyacetamide (3 g., 15 mmoles) was taken into 40 ml. of tert-butanol and dimethyl carbonate (2.7 g., 2.5 ml. 30 mmoles). Potassium tert-butoxide (3.4 g., 30 mmoles) was added portionwise and the reaction mixture heated to reflux for 65 minutes, cooled to room temperature, quenched by the portionwise addition of 60 ml. of 1 N hydrochloric acid, poured into 200 ml. of water and extracted with three portions of ethyl acetate. The combined organic extracts were washed with water, washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield 5-(2-chloro-6-fluorophenyl)oxazolidine-2,4-dione (3.5 g.). Purified product was obtained by recrystallization from toluene (3.0 g., m.p. 156°-158° C.).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 65 minutes
  3. customquenched by the portionwise addition of 60 ml
  4. additionof 1 N hydrochloric acid, poured into 200 ml
  5. extractionof water and extracted with three portions of ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-153efbecb30949b89233fbaf1838fdae
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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