4-Chlorobenzoyl chloride → HCID 20284819, Verbindung

HRID 127521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127521
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[S:14][CH2:13][CH2:12]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:31](=[O:32])[C:30]3[CH:34]=[CH:35][C:27]([Cl:26])=[CH:28][CH:29]=3)[C:15]=2[S:14][CH2:13][CH2:12]1)[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 85014-Chlorobenzoyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 202847894-(N-t-Butoxycarbonyl-N-methylaminomethyl)2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Produkt 1

HCID 20284819HCID 20284819, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of the product (333 mg) of the above (1) in dimethylformamide (8 ml) is added a 50% suspension (58 mg) of sodium hydride in mineral oil. The mixture is stirred at room temperature for 1 hour and further at 40°-50° C. for 30 minutes. After addition of a solution of p-chlorobenzoyl chloride (210 mg) in dimethylformamide (2 ml) under ice-cooling, the mixture is further stirred at room temperature for 2 hours. A 10% aqueous solution of ammonium chloride (10 ml) is added thereto under ice-cooling. The mixture is extracted with chloroform. The extract is washed with an aqueous solution of sodium bicarbonate and water, dried and evaporated to give 4-(N-t-butoxycarbonyl-N-methylaminomethyl)-9-(p-chlorobenzoyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole as an oil (533 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture is further stirred at room temperature for 2 hours
  3. temperatureunder ice-cooling
  4. extractionThe mixture is extracted with chloroform
  5. washThe extract is washed with an aqueous solution of sodium bicarbonate and water
  6. customdried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5535ce880c8b4b2cb013bb240bc2c98c
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256640

Notizen zur Reaktion

Wird geladen…