Dimethylhydantoin → Nilutamide

HRID 374122

Reaktionsgleichung

Reaktionsgleichung von HRID 374122
C1(OC2C=CC=CC=2)C=CC=CC=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20](Cl)=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25])([O-:16])=[O:15].[CH3:28][C:29]1([CH3:36])[NH:33][C:32](=[O:34])[NH:31][C:30]1=[O:35]>>[F:25][C:24]([F:27])([F:26])[C:18]1[CH:19]=[C:20]([N:31]2[C:30](=[O:35])[C:29]([CH3:36])([CH3:28])[NH:33][C:32]2=[O:34])[CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15]

Komponenten

4

Edukt 3

HCID 6491DimethylhydantoinHCID 7583Diphenyl EtherHCID 670525-Chloro-2-nitrobenzotrifluoride

Produkt 1

HCID 4493NilutamideAusbeute 21 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

The following were introduced into 383.52 ml of phenyl oxide: 225.60 grams of 2-nitro-5-chloro-trifluoromethylbenzene, described in the German Patent No. DRP 637,318, 128.10 grams of 5,5-dimethylhydantoin described in Beil., Vol. 24, 289 and 198.53 grams of cuprous oxide. The mixture was heated to 200° C. for 24 hours, then cooled to 20° C. and filtered. The residue was rinsed with phenyl oxide, then extracted with ethyl acetate. The ethyl acetate phase was concentrated to dryness under reduced pressure at 60° C. and the residue was taken up in ammoniacal dichloroethane. The crystals obtained were dried at 60° C. to obtain 66.55 grams of crude product which, after purification from aqueous ethanol yielded 62.55 grams of purified desired product.

Aufarbeitung

  1. temperaturecooled to 20° C.
  2. filtrationfiltered
  3. washThe residue was rinsed with phenyl oxide
  4. extractionextracted with ethyl acetate
  5. concentrationThe ethyl acetate phase was concentrated to dryness under reduced pressure at 60° C.
  6. customThe crystals obtained
  7. customwere dried at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-c6995796f7544ecf97ce6299cba7727e
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166358

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