Dimethylhydantoin → Nilutamide

HRID 374124

Reaction equation

HRID 374124 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[CH3:15][C:16]1([CH3:23])[NH:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].[OH-].[K+]>CS(C)=O>[F:12][C:11]([F:14])([F:13])[C:5]1[CH:6]=[C:7]([N:18]2[C:17](=[O:22])[C:16]([CH3:23])([CH3:15])[NH:20][C:19]2=[O:21])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 14797Potassium HydroxideHCID 670525-Chloro-2-nitrobenzotrifluoride

Product 1

HCID 4493Nilutamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
110 °C

Procedure

30 ml of dimethylsulfoxide and 24.8 grams of 2-nitro-5-chloro trifluoromethylbenzene were introduced at 20° C. with stirring into 100 ml of dimethylsulfoxide, 12.80 grams of 5,5-dimethyl-hydantoin and 6.28 grams of potassium hydroxide in the form of flakes. The mixture was heated to 110° C. for a period of time variable between 3 and 18 hours. The product was characterized and determined by thin layer chromatography.

Sources & evidence

ORD record
ord-2ae4db263d7146fbaf6b90c5a74f8452
Source dataset
uspto-grants-1992_11
Patent number
US05166358

Linked notes

Loading…