p-Toluenesulfonic acid → {2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

HRID 1797303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797303
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22])[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10118970(2-Chloro-4-{[2-({2-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]ethoxy}methyl)phenyl]amino}phenyl)(2-methylphenyl)methanone

Produkt 1

HCID 10203602{2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Compound 149 (5.68 g, 10.8 mmol) was dissolved in MeOH (100 mL) and p-toluenesulfonic acid (3.09 g, 16.3 mmol) was added. The solution was stirred at room temperature for 2 h. Aqueous NaHCO3 (5%, 100 mL) was added and the water phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/Petroleum ether 1:1–3:2 as the eluent to afford the title compound as an orange oil.

Aufarbeitung

  1. extractionthe water phase was extracted with EtOAc (3×50 mL)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a5b4afd97664151bbbb237180954c8c
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034015B2

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