Diethyl Carbonate → HCID 13770526, Verbindung

HRID 236366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236366
[H-].[Na+].[C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17](=[O:20])[CH2:16]2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:21](=O)([O:25]CC)[O:22][CH2:23][CH3:24]>CN(C)C=O>[C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17](=[O:20])[CH:16]2[C:21]([O:22][CH2:23][CH3:24])=[O:25])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 1709837-Benzoyl-2-oxindole

Produkt 1

HCID 13770526HCID 13770526, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of 365 mg. of sodium hydride in 8 ml. of dimethylformamide at 0° C. was gradually added 1.0 g. (4.22 mmoles) of 7-benzoyloxindole, and the mixture allowed to stir for 10 minutes in an ice bath. Diethyl carbonate (1.53 g., 12.7 mmoles) was added and the reaction mixture allowed to stir at ice bath temperatures for 3 hours. The mixture was then poured into 200 ml. of ice and water and the resulting precipitate filtered, washed with water and vacuum dried, 940 mg. The crude product was slurried in diethyl ether, filtered and the filtrate extracted with 0.1N aqueous sodium hydroxide solution. The base layer was separated and acidified with hydrochloric acid. The resulting precipitate was filtered and dried, 109 mg., m.p. 134° C. (dec.).

Aufarbeitung

  1. customat 0° C.
  2. stirringto stir at ice bath temperatures for 3 hours
  3. additionThe mixture was then poured into 200 ml
  4. filtrationof ice and water and the resulting precipitate filtered
  5. washwashed with water and vacuum
  6. customdried
  7. filtrationfiltered
  8. extractionthe filtrate extracted with 0.1N aqueous sodium hydroxide solution
  9. customThe base layer was separated
  10. filtrationThe resulting precipitate was filtered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-942ab94e918a4ca6bd5a5402a41848fc
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04644005

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