N,N'-Dimethylethylenediamine → 4-(5-Methyl-2-oxooxazolidin-3-yl)benzoic acid

HRID 1803975Notes

Reaction equation

HRID 1803975 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH3:13][CH:14]1[O:18][C:17](=[O:19])[NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:13][CH:14]1[O:18][C:17](=[O:19])[N:16]([C:2]2[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=2)[CH2:15]1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 1368375-Methyl-2-oxazolidinoneHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 584848664-(5-Methyl-2-oxooxazolidin-3-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1-amino-2-propanol (1.4 g), diethyl carbonate (2.4 mL) and potassium carbonate (500 mg) was stirred at 150° C. for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give 5-methyloxazolidin-2-one (1.9 g). To a mixture of ethyl 4-iodobenzoate (3.2 mL), 5-methyloxazolidin-2-one (1.9 g), potassium carbonate (8 g) and copper (I) iodide (720 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (800 μL), and the mixture was refluxed for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in methanol (20 mL) and 1,4-dioxane (20 mL), 1N aqueous sodium hydroxide solution (40 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1N hydrochloric acid (40 mL) was added, and the mixture was extracted with chloroform. The solvent was evaporated to give the title compound (3.9 g).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in methanol (20 mL)
  7. addition1,4-dioxane (20 mL), 1N aqueous sodium hydroxide solution (40 mL) was added
  8. addition1N hydrochloric acid (40 mL) was added
  9. extractionthe mixture was extracted with chloroform
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a543a64a6ac145b09042ce77a5165038
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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