Glycerol → HCID 19381206, 화합물

HRID 2063543노트

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HRID 2063543 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 19381206HCID 19381206, 화합물수율 68.8%

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

반응 조건

온도
135 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-01baaf861b674837b307edb9a432574d
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288373B2

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