Hydrochloric Acid → HCID 9885335, Verbindung

HRID 581091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581091
[C:1]([C:4]1[CH:5]=[C:6]([C:9]([OH:11])=O)[S:7][CH:8]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([NH2:36])=[O:35])[C:29](=[O:37])[CH2:28]2.Cl>CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([NH2:36])=[O:35])[C:29](=[O:37])[CH:28]2[C:9](=[O:11])[C:6]1[S:7][CH:8]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 131564014-Acetylthiophene-2-carboxylic acid

Produkt 1

HCID 9885335HCID 9885335, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A 0.78 g (4.59 nmuoles) sample of 4-acetyl-2-thio-phenecarboxylic acid (prepared according to Satonaka, H., Bull. Chem. Soc. Japan 56:2463 (1983)) was combined with 0.95 g (5.85 mmoles) of 1,1'-carbonyldiimidazole in 10 ml of N,N-dimethylformamide and stirred at room temperature under argon atmosphere. After two hours the reaction contents were transferred to an addition funnel and slowly added to a slurry of 0.88 g (4.18 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 1.38 g (11.28 mmoles) of 4-(N,N-dimethylamino)pyridine in 30 ml of N,N-dimethylformamide stirring at 5° C. (ice bath) under an inert atmosphere. The reaction contents were stirred for fifteen minutes at 5° C. after complete addition followed by twenty-four hours at room temperature. Pouring the reaction mixture into 110 ml of 0.3N hydrochloric acid cause the precipitation of a greenish-yellow solid. Filtration followed by sequential washing with 3N hydrochloric acid and water, provided the crude product which was recrystallized twice from acetic acid to give 0.34 g (0.94 mmoles, 22% yield) of pure 5-chloro-3-(4-acetyl-2-thenoyl)-2-oxindole-1-carboxamide as a greenish-yellow solvated complex with 0.2 equivalents of acetic acid, m.p. 230-233° C.

Aufarbeitung

  1. customAfter two hours the reaction contents
  2. customwere transferred to an addition funnel
  3. customThe reaction contents
  4. stirringwere stirred for fifteen minutes at 5° C.
  5. additionafter complete addition
  6. waitfollowed by twenty-four hours at room temperature
  7. customthe precipitation of a greenish-yellow solid
  8. filtrationFiltration
  9. washby sequential washing with 3N hydrochloric acid and water
  10. customprovided the crude product which
  11. customwas recrystallized twice from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-11d033a1dd54416785647c3a19a8fd20
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919809

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