N,N'-Dimethylethylenediamine → Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoate

HRID 1803943ノート

反応式

HRID 1803943 の反応式
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[O:18]=[C:14]1[N:15]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16][CH2:17][O:13]1

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 142891Ethyl 4-iodobenzoate

生成物 1

HCID 616604Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a mixture of ethyl 4-iodobenzoate (1.5 mL), oxazolidin-2-one (940 mg), potassium carbonate (2.5 g) and copper (I) iodide (171 mg) were added toluene (9 mL) and N,N′-dimethylethylenediamine (195 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. The residue was purified by column chromatography (chloroform) to give the title compound (1.2 g).

後処理

  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
  6. customThe residue was purified by column chromatography (chloroform)

出典と根拠

ORDレコード
ord-9fc62e2fb21f470c88216cdd48a9e957
出典データセット
uspto-grants-2013_01
特許番号
US08354401B2

反応ノート

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