Dimethylhydantoin → Nilutamide

HRID 374123

Reaction equation

HRID 374123 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 4493NilutamideYield 30%

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e1a261677b474525b612c97fa3ced3ef
Source dataset
uspto-grants-1992_11
Patent number
US05166358

Linked notes

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