Nilutamide → 1-(4-Nitro-3-trifluoromethyl-phenyl)-3,4,4-trimethyl-2,5-imidazolidinedione
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]2=[O:20])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:25]I>CN(C)C=O>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[N:14]([CH3:25])[C:13]2=[O:20])=[CH:4][C:3]=1[C:2]([F:1])([F:21])[F:22])([O-:11])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3.17 g of 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl-imidazoline-2,5-dione (French Patent No. 2,329,276) and 32 ml of dimethylformamide were added at 23° C. to 26° C. to a 50% suspension of 492 mg of sodium hydride in oil and 3 ml of dimethylformamide and after stirring for 15 minutes, a solution of 0.7 ml of methyl iodide in 2 ml of dimethylformamide was added. The mixture was stirred for 25 minutes at 24° C. to 28° C. and was then poured into 200 g of a 1-1 water-ice mixture. The mixture was extracted with ether and the organic phase was washed with saturated aqueous sodium chloride, dried, filtered and evaporated to dryness under reduced pressure to obtain 3.6 g of the desired product melting at 116° C. An analytical sample was crystallized from isopropyl alcohol to obtain 2.73 g of the product melting at 116° C.
Workup
- stirringThe mixture was stirred for 25 minutes at 24° C. to 28° C.
- extractionThe mixture was extracted with ether
- washthe organic phase was washed with saturated aqueous sodium chloride
- customdried
- filtrationfiltered
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-9645f82cccb74d1ea938c1c9e5f3261b
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05627201
Reaction notes
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