Acetamide → HCID 13092002, compound

HRID 1163939Notes

Reaction equation

HRID 1163939 reaction equation
C[C:2](C)([O-:4])C.[K+].C(O)C.C(=O)(OCC)OCC.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:30][CH3:31])=[C:23]([CH:25]([OH:29])[C:26]([NH2:28])=[O:27])[CH:24]=1.C(N)(=O)C.Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:30][CH3:31])=[C:23]([CH:25]2[O:29][C:2](=[O:4])[NH:28][C:26]2=[O:27])[CH:24]=1

Participants

9

Reactant 6

HCID 178AcetamideHCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl Carbonate2×HCID 13093555HCID 13093555, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 13092002HCID 13092002, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert.-butoxide (539 mg., 4.8 mmoles) was dissolved in ethanol (2.12 g., 2.65 ml., 4.6 moles). Diethyl carbonate (625 mg., 5.3 mmoles) and then 2-(5-chloro-2-methoxyphenyl)-2-hydroxyacetamide (1.0 g., 4.6 mmoles) were added and the mixture was stirred for a few minutes to achieve solution, and then heated to reflux for 16 hours, at which time tlc (1:1 ethyl acetate:chloroform) indicated some unreacted starting material. Addition of more diethyl carbonate (625 mg.) and potassium tert-butoxide (100 mg.) and a further 2.5 hours of reflux did not appear to significantly reduce the level of starting acetamide. The reaction mixture was cooled to room temperature, poured into excess, iced 1 N hydrochloric acid and extracted with three portions of chloroform. The combined chloroform extracts were extracted with excess 5% sodium bicarbonate in two portions. The combined bicarbonate extracts were poured slowly into excess 1 N hydrochloric acid to precipitate 5-(5-chloro-2-methoxyphenyl)oxazolidine-2,4-dione (430 mg. 39%; m.p. 179°-181° C.).

Workup

  1. temperatureheated
  2. temperaturea further 2.5 hours of reflux
  3. extractionextracted with three portions of chloroform
  4. extractionThe combined chloroform extracts were extracted with excess 5% sodium bicarbonate in two portions
  5. additionThe combined bicarbonate extracts were poured slowly into excess 1 N hydrochloric acid
  6. customto precipitate 5-(5-chloro-2-methoxyphenyl)oxazolidine-2,4-dione (430 mg. 39%; m.p. 179°-181° C.)

Sources & evidence

ORD record
ord-8521887c1f874d20ba9c80b8a99a6f2e
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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