Nilutamide → 5,5-Dimethyl-3-(4-nitro-3-trifluoromethyl-phenyl)-1-nonyl-2,4-imidazolidinedione

HRID 35938

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+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>>[CH3:18][C:15]1([CH3:19])[N:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:13](=[O:20])[N:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)[C:16]1=[O:17]

Participants

Reactant 3

HCID 4493Nilutamide

HCID 127421-Bromononane

HCID 24758Sodium hydride

Product 1

HCID 221169515,5-Dimethyl-3-(4-nitro-3-trifluoromethyl-phenyl)-1-nonyl-2,4-imidazolidinedione

Procedure

Using the procedure of Example 1, 1 g of 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl imidazolidine-2,5-dione was reacted with a 50% suspension of 170 mg of sodium hydride in oil and 0.7 ml of 1-bromo-nonane to obtain after chromatography on silica 1.08 g of the desired product melting at 63° C.

Sources & evidence

ORD record: ord-ff946c18220b4bed99f4df292ed2a703
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411981

Linked notes

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