4-Aminothiophenol → 2-(4-Aminophenylthio)-6-methoxyquinoline

HRID 55068

Reaktionsgleichung

Reaktionsgleichung von HRID 55068
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.CN(C1C=CC=CN=1)C>C(O)C>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[N:3]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 145104-AminothiophenolHCID 218852-DimethylaminopyridineHCID 836472-Chloro-6-methoxyquinoline

Produkt 1

HCID 189716622-(4-Aminophenylthio)-6-methoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Chloro-6-methoxyquinoline (52.0 mmoles, 10.0 g), 4-aminothiophenol (52.0 mmoles, 6.5 g) and dimethylaminopyridine (52.0 mmoles, 6.3 g) were stirred for 16 hr in 250 ml ethanol. The reaction was condensed and purified by HPLC over silica gel eluted with 25-30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)-6-methoxyquinoline. 8.5 g, 58% product. Mass spec (FD) 282. Calculated for C16H14N2OS: C, 68.06; H, 5.00, N, 9.92. Found: C, 68.04; H, 4.97; N, 10.02.

Aufarbeitung

  1. customcondensed
  2. custompurified by HPLC over silica gel
  3. washeluted with 25-30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-08c795c675d44ec988099b77cf02e9b6
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624937

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