Ethyl Acetate → 6,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline

HRID 387846

Reaktionsgleichung

Reaktionsgleichung von HRID 387846
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[S:15].Br[C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1.C(OCC)(=O)C.[OH-].[Na+]>CN(C)C=O.CCCCCC>[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:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 182112-Bromo-5-nitrothiazoleHCID 229368096,7-Dimethoxyquinoline-4(1H)-thione

Produkt 1

HCID 229367196,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinolineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

After suspending 6,7-dimethoxy-1H-quinoline-4-thione (2.21 g, 10.0 mmol) in dimethylformamide (30 ml), 2-bromo-5-nitrothiazole (2.30 g, 11.0 mmol) was added at 0° C., and then the mixture was stirred at room temperature for 1 hour. The reaction solution was distributed between ethyl acetate and 1N aqueous sodium hydroxide, the organic layer was washed with water and saturated saline 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:hexane=3:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (1.70 g, 4.87 mmol, 49%) as light yellow crystals.

Aufarbeitung

  1. additionwas added at 0° C.
  2. washthe organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. customThe obtained crude product
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additiondiluted with hexane
  10. filtrationafter which the crystals were filtered out
  11. washwashed with hexane
  12. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-0cde1c2d547b47779348d45db479b3da
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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