Tetrahydrofuran → 2-(4-Aminophenylthio)-4-phenylquinoline

HRID 55066

Reaktionsgleichung

Reaktionsgleichung von HRID 55066
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1.C1COCC1>CN(C1C=CN=CC=1)C.C(O)C>[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][C:2]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 145104-AminothiophenolHCID 23066872-Chloro-4-phenylquinoline

Produkt 1

HCID 189716782-(4-Aminophenylthio)-4-phenylquinolineAusbeute 451,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Chloro-4-phenylquinoline (4.18 mmoles, 10.0 g), 4-aminothiophenol (41.8 mmoles, 5.2 g) and DMAP (41.8 mmoles, 5.0 g) were stirred in 200 ml ethanol and 50 ml THF for 3 days. The solution was concentrated, ethyl acetate added, washed with water, dried over sodium sulfate and the solvent removed. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-4-phenylquinoline 6.2 g, 45%. Mass Spec (FD) 328. Calculated for C21H16N2S: C, 76.80; H, 4.91 N, 8.53. Found: C, 77.04; H, 5.00; N, 8.55.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. additionethyl acetate added
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed
  6. customThe product was purified by HPLC over silica gel
  7. washeluted with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ddb4f227ade34c0fa23ac2005f0389d6
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624937

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