Potassium Carbonate → 3-[2-(5-Methoxy-2-methyl-phenylamino)-ethyl]-oxazolidin-2-one

HRID 270767ノート

反応式

HRID 270767 の反応式
C1(C)C=CC(S(O[CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])(=O)=O)=CC=1.[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:22]=1[NH2:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:21]([CH3:20])=[C:22]([NH:23][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])[CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 995005-Methoxy-o-toluidineHCID 157609472-(2-Oxooxazolidin-3-yl)ethyl 4-methylbenzenesulfonate

生成物 1

HCID 210711283-[2-(5-Methoxy-2-methyl-phenylamino)-ethyl]-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a flask was added 2.95 g (10.3 mmol) of Toluene-4-sulfonic acid, 2-(2-oxo-oxazolidin-3-yl)-ethyl ester, 1.56 g (11.4 mmol) of 2-methyl-5-methoxyaniline, 2.58 g (18.7 mmol) of potassium carbonate, and 22 mL of anhydrous dimethylformamide, and the mixture was heated at 100° C. for seven hours. The reaction was allowed to cool to room temperature, and was partitioned between ethyl acetate and water. The phases were separated, and the ethyl acetate phase was washed with brine, dried over Na2SO4, filtered, and concentrated to an oil. The oil was purified by chromatography (120 mL silica, 60 ethyl acetate/40 hexanes) to give the corresponding product as a clear oil that solidified upon drying: 1H NMR (DMSO-d6, 400 MHz) 6.81 (d, 1H), 6.11 (s, 1H), 6.04 (d, 1H), 4.92 (t, 1H), 4.21 (t, 2H), 3.65 (s, 3H), 3.59 (m, 2H), 3.31 (m, 2H), 3.23 (m, 2H), 1.95 (s, 3H) ppm.

後処理

  1. temperatureto cool to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe ethyl acetate phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by chromatography (120 mL silica, 60 ethyl acetate/40 hexanes)

出典と根拠

ORDレコード
ord-14833e54d0ac45178dcb387a4d6a3809
出典データセット
uspto-grants-2008_11
特許番号
US07449576B1

反応ノート

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