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

HRID 389887Notes

Reaction equation

[O:1]=[C:2]1[NH:6][C:5]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:20])[NH:3]1.Br[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=1>CC(N(C)C)=O.[Cu]=O>[C:15]([C:14]1[CH:13]=[C:12]([C:5]2([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:20])[N:3]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([C:30]([F:31])([F:33])[F:32])[CH:23]=3)[C:2](=[O:1])[NH:6]2)[CH:19]=[CH:18][CH:17]=1)#[N:16]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 579 mg of 3-[2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-4-yl]benzonitrile and 534 mg of 4-bromo-2-(trifluoromethyl)benzonitrile in DMAC (2.5 mL), 183 mg of copper oxide are added. The mixture is refluxed overnight at 130° C. The mixture is concentrated, taken in DCM, washed with a solution of 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 solution of 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-7193ee21aa37467686ff14846edefe66
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383608B2

Reaction notes

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