Acetamide → HCID 13092002, compound

HRID 544306Notes

Reaction equation

HRID 544306 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 lN 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 lN 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 lN 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-4054279d528d44b682cac59f3eba4fb3
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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