Ethanol → 2-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiazol-5-ylamine

HRID 1010234

Reaktionsgleichung

Reaktionsgleichung von HRID 1010234
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([N+:21]([O-])=O)=[CH:19][N:20]=1.[Cl-].[NH4+].C(O)C.O>[Fe].CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([NH2:21])=[CH:19][N:20]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 229367196,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline

Produkt 1

HCID 229363012-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiazol-5-ylamineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

After suspending 6,7-dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline (699 mg, 2.00 mmol), iron (559 mg, 10.0 mmol) and ammonium chloride (1.07 g, 20.0 mmol) in an ethanol (20 ml)-water (5 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 20 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in an ethyl acetate-tetrahydrofuran mixed solvent. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:methanol=30:1), and the fraction containing the target substance was concentrated to obtain the title compound (190 mg, 0.595 mmol, 30%) as yellowish-brown crystals.

Aufarbeitung

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in an ethyl acetate-tetrahydrofuran mixed solvent
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. additionthe fraction containing the target substance
  12. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6773266bd2a147278f3696ba6901f93e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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