Glycerol → HCID 19381206、化合物

HRID 2063543ノート

反応式

HRID 2063543 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].[CH2:11](O)[CH:12](O)[CH2:13]O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[OH-].[Na+]>CS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]2[C:3]=1[N:10]=[CH:13][CH:12]=[CH:11]2

参加物

6

反応物 4

HCID 753GlycerolHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 106318572-Bromo-4-ethylaniline

生成物 1

HCID 19381206HCID 19381206、化合物収率 68.8%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
135 °C

実験手順

A mixture of 2-bromo-4-ethylphenylamine (1.6 g, 8.0 mmol), propane-1,2,3-triol (1.84 g, 2.5 equiv), FeSO4 (0.067 g, 0.30 equiv), 3-nitrobenzenesulfonic acid sodium salt (1.13 g, 0.63 equiv) in 4.5 mL of methanesulfonic acid was heated at 135° C. for 3 hours and then cooled to room temperature. 2 N Aqueous NaOH (˜40 mL) was added and the mixture was extracted with EtOAc (3×50 mL). The organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel flash column chromatography using 5% to 20% EtOAc in hexane to afford the title compound as a black solid (1.3 g). MS (ES) m/z 235.9 (M+H+).

後処理

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-01baaf861b674837b307edb9a432574d
出典データセット
uspto-grants-2012_10
特許番号
US08288373B2

反応ノート

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