N,N'-Dimethylethylenediamine → Ethyl 4-(5-methoxymethyl-2-oxooxazolin-3-yl)benzoate

HRID 1803974Notes

Reaction equation

HRID 1803974 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[NH:6][CH2:5]1.I[C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[O:8][C:7](=[O:9])[N:6]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 103131495-(Methoxymethyl)oxazolidin-2-one

Product 1

HCID 67380766Ethyl 4-(5-methoxymethyl-2-oxooxazolin-3-yl)benzoate

Reagents, catalysts & solvents 3

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

Procedure

By reaction and treatment in the same manner as in Preparation Example 25 and using 1-amino-3-methoxypropan-2-ol (1 g), 5-methoxymethyloxazolidin-2-one (620 mg) was obtained. To a mixture of 5-methoxymethyloxazolidin-2-one (620 mg), ethyl 4-iodobenzoate (1.6 mL), potassium carbonate (2.6 g) and copper (I) iodide (552 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (625 μL), and the mixture was refluxed for 8 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 the title compound (830 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6474c16a1aa34b2085516384c64e2fbd
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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