Water → 5-Chloro-[1,3,4]thiadiazole-2-carboxylic Acid (7-chloro-quinolin-4-yl)-amide

HRID 916623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916623
[H-].[Na+].[NH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[Cl:15][C:16]1[S:20][CH:19]=[N:18][N:17]=1.O.CN([CH:25]=[O:26])C>>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:4]([NH:3][C:25]([C:19]3[S:20][C:16]([Cl:15])=[N:17][N:18]=3)=[O:26])=[CH:5][CH:6]=[N:7]2)=[CH:12][CH:11]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 947117-Chloro-4-aminoquinolineHCID 129564682-Chloro-1,3,4-thiadiazole

Produkt 1

HCID 589612375-Chloro-[1,3,4]thiadiazole-2-carboxylic Acid (7-chloro-quinolin-4-yl)-amideAusbeute 60 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

NaH (0.023 g, 0.58 mmol) was added in portions to a solution of 4-amino-7-chloro-quinoline (0.1 g, 0.56 mmol) in DMF (6 ml) at room temperature and the mixture was stirred for 20 min. 5-Chloro-[1,3,4]thiadiazole derivative (0.108 g, 0.56 mmol) was then added in one portion and the mixture heated at 80° C. (oil bath temperature) for 18 h. The reaction mixture was allowed to cool to room temperature and water (15 ml) was added. The precipitate was separated by filtration, washed with Et2O and dried to afford the product (0.08 g, 60% yield).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe precipitate was separated by filtration
  3. washwashed with Et2O
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5f21aeb908974aae92e2e6f06e197dbf
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271179B2

Notizen zur Reaktion

Wird geladen…