Dimethylhydantoin → Nilutamide

HRID 374123

Reaktionsgleichung

Reaktionsgleichung von HRID 374123
COCCOCCOCCOC.[N+:13]([C:16]1[CH:21]=[CH:20][C:19](Cl)=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24])([O-:15])=[O:14].[CH3:27][C:28]1([CH3:35])[NH:32][C:31](=[O:33])[NH:30][C:29]1=[O:34]>>[F:24][C:23]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([N:30]2[C:29](=[O:34])[C:28]([CH3:35])([CH3:27])[NH:32][C:31]2=[O:33])[CH:20]=[CH:21][C:16]=1[N+:13]([O-:15])=[O:14]

Komponenten

4

Edukt 3

HCID 6491DimethylhydantoinHCID 8189TriglymeHCID 670525-Chloro-2-nitrobenzotrifluoride

Produkt 1

HCID 4493NilutamideAusbeute 30 %

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

The following were introduced into 282 ml of triglyme: 112.8 grams of 2-nitro-5-chloro-trifluoromethylbenzene, 64.1 grams of 5,5-dimethyl-hydantoin and 33.5 grams of cuprous oxide. The mixture was heated to about 215° C.±5° C. for 4 hours, then cooled to 20° C. and filtered. The triglyme solution was recovered and a 22 Be ammonia solution (1V), toluene (1V) and demineralized water (4V) were added to the solution of triglyme (1V). The solution was stirred at 20° C. for 15 minutes, then cooled to about -10° C. and stirred again at -10° C. After washing and drying, 47.6 grams of the desired product were obtained.

Aufarbeitung

  1. temperatureThe mixture was heated to about 215° C.±5° C. for 4 hours
  2. filtrationfiltered
  3. customThe triglyme solution was recovered
  4. additiona 22 Be ammonia solution (1V), toluene (1V) and demineralized water (4V) were added to the solution of triglyme (1V)
  5. temperaturecooled to about -10° C.
  6. stirringstirred again at -10° C
  7. washAfter washing
  8. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-e1a261677b474525b612c97fa3ced3ef
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166358

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