4-Bromo-2-(trifluoromethyl)benzonitrile → 4-[2,5-Dioxo-4-(3-methylphenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389897Notes

Reaction equation

[CH2:1]([O:4][CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7]1)[CH:2]=[CH2:3].Br[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=1>CC(N(C)C)=O.[Cu-]=O>[O:12]=[C:8]1[NH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)([CH2:5][O:4][CH2:1][CH:2]=[CH2:3])[C:10](=[O:11])[N:9]1[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:30])([F:32])[F:31])[CH:22]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-[(2-propenyloxy)methyl]-4-(3-methylphenyl)imidazolidine-2,5-dione (899 mg) and 4-bromo-2-(trifluoromethyl)benzonitrile (863 mg) in DMAC (5 mL) is added copper (I) oxide (395 mg). The mixture is refluxed overnight at 130° C. The mixture is concentrated, taken in ethyl acetate, washed with a 10% aqueous ammonia solution and brine. The organic phase is dried over magnesium sulfate, concentrated under vacuum and purified on silica gel (ethyl acetate/cyclohexane 0/100 to 50/50) to give the desired compound.

Workup

concentrationThe mixture is concentrated
washwashed with a 10% aqueous ammonia solution and brine
dry with materialThe organic phase is dried over magnesium sulfate
concentrationconcentrated under vacuum
custompurified on silica gel (ethyl acetate/cyclohexane 0/100 to 50/50)

Sources & evidence

ORD record: ord-e8e8753c11a04cfba64806ae8c60274c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383608B2

Reaction notes

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