Dimethylhydantoin → Nilutamide

HRID 374125

Reaction equation

HRID 374125 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[N+:10]([C:13]1[CH:18]=[CH:17][C:16](Cl)=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21])([O-:12])=[O:11]>C(O)C.[Cu]>[F:21][C:20]([F:22])([F:23])[C:14]1[CH:15]=[C:16]([N:4]2[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]2=[O:7])[CH:17]=[CH:18][C:13]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 6491DimethylhydantoinHCID 670525-Chloro-2-nitrobenzotrifluoride

Product 1

HCID 4493Nilutamide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
200 °C

Procedure

71.5 grams of copper in powder form were added to 96.10 grams of 5,5-dimethyl-hydantoin and 170.86 grams of 2-nitro-5-chloro trifluoromethylbenzene. The mixture was heated to 200° C. for about 21 hours, the pressure being maintained at 450 millibars, then, was cooled to 20° C. and taken up in 480 ml of ethanol. The product was characterized and determined by thin layer chromatography of the ethanol solution.

Workup

  1. temperaturethe pressure being maintained at 450 millibars
  2. temperaturewas cooled to 20° C.

Sources & evidence

ORD record
ord-f33c2a567db743aeaaf8f1ed8c025a89
Source dataset
uspto-grants-1992_11
Patent number
US05166358

Linked notes

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