Chlorotriethylsilane → HCID 22714347, Verbindung

HRID 351776

Reaktionsgleichung

Reaktionsgleichung von HRID 351776
C([Li])CCC.[CH3:6][N:7]([CH3:16])[S:8]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)(=[O:10])=[O:9].Cl[Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20].[Cl:25][C:26]1[CH:51]=[CH:50][C:29]([C:30]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]([CH3:42])[C:37](=[O:43])[CH:36]=[C:35]3[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:31])=[CH:28][CH:27]=1>O1CCCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]([CH3:42])[C:37](=[O:43])[CH:36]=[C:35]3[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([OH:31])[C:14]2[N:13]=[C:12]([Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[N:11]([S:8]([N:7]([CH3:16])[CH3:6])(=[O:9])=[O:10])[CH:15]=2)=[CH:50][CH:51]=1

Komponenten

6

Edukt 4

HCID 13819ChlorotriethylsilaneHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 22714346HCID 22714346, VerbindungHCID 178418339Butyllithium2×

Produkt 1

HCID 22714347HCID 22714347, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Butyllithium (30.1 ml) was added slowly at −78° C. to a solution of N,N-dimethyl-1H-imidazol-1-sulfonamide (8,4 g) in tetrahydrofuran (150 ml) and the mixture was stirred at −78° C. for 15 minutes. Chlorotriethylsilane (8.1 ml) was added and the mixture was stirred till the temperature reached 20° C. The mixture was cooled till −78° C., butyllithium (30.1 ml) was added, the mixture was stirred at −78° C. for 1 hour and allowed to reach −15° C. The mixture was cooled again till −78° C., a solution of 6-(4-chlorobenzoyl)-1-methyl-4-phenyl-2(1H)-quinolinone (15 g) in tetrahydrofuran (30 ml) was added and the mixture was stirred till the temperature reached 20° C. The mixture was hydrolized and extracted with ethyl acetate. The organic layer was dried, filtered off and evaporated till dryness. The product was used without further purification, yielding 26 g (100%) of (±)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-2-(triethylsilyl)-1H-imidazole-1-sulfonamide (interm. 3-a).

Aufarbeitung

  1. stirringthe mixture was stirred till the temperature
  2. customreached 20° C
  3. temperatureThe mixture was cooled till −78° C.
  4. stirringthe mixture was stirred at −78° C. for 1 hour
  5. customto reach −15° C
  6. temperatureThe mixture was cooled again till −78° C.
  7. stirringthe mixture was stirred till the temperature
  8. customreached 20° C
  9. extractionextracted with ethyl acetate
  10. customThe organic layer was dried
  11. filtrationfiltered off
  12. customevaporated till dryness
  13. customThe product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-e6fc411faa16427690fdf219e21c4fae
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743805B2

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