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Triethylamine → N-(2-Dimethylaminopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

HRID 1830426
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Reaktionsgleichung

Reaktionsgleichung von HRID 1830426
[NH2:1][C:2]1[C:3]([N:8]([CH3:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:27][O:28][C:29]1[C:30](=[O:53])[C:31]([CH3:52])=[C:32]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:48][C:49](=[O:51])[CH3:50])=[C:43]([CH:47]=2)[C:44](O)=[O:45])[C:33](=[O:37])[C:34]=1[O:35][CH3:36]>C(Cl)Cl>[CH3:9][N:8]([CH3:10])[C:3]1[C:2]([NH:1][C:44](=[O:45])[C:43]2[CH:47]=[C:39]([CH2:38][C:32]3[C:33](=[O:37])[C:34]([O:35][CH3:36])=[C:29]([O:28][CH3:27])[C:30](=[O:53])[C:31]=3[CH3:52])[CH:40]=[CH:41][C:42]=2[O:48][C:49](=[O:51])[CH3:50])=[CH:7][CH:6]=[CH:5][N:4]=1
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 15656134N2,N2-Dimethyl-2,3-pyridinediamineHCID 220542715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic Acid

Produkt 1

HCID 22054319N-(2-Dimethylaminopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide
Ausbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Amino-2-dimethylaminopyridine (0.154 g, 1.125 mmol), triethylamine (0.114 g, 1.125 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.190 g, 1.125 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.281 g, 0.750 mmol) and the resulting solution was stirred at room temperature for 4 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=95:5) to obtain the titled compound (0.139 g, 0.282 mmol, 38%).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-cce376bd631d4004b75ba448a9473c89
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07064124B2

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