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

HRID 2427135Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([CH2:28][O:29][CH2:30][CH:31]=[CH2:32])[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22]2)=[CH:17][CH:16]=1>CC(N(C)C)=O.N.[Cu-]=O>[O:27]=[C:23]1[NH:22][C:21]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)([CH2:28][O:29][CH2:30][CH:31]=[CH2:32])[C:25](=[O:26])[N:24]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

0.33 g of copper (I) oxide and 0.95 g of 4-bromo-2-trifluoromethylbenzonitrile are added to a solution of 1 g 4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidine-2,5-dione obtained in step 3 in 3 mL of DMAC. The mixture is heated at 160° C. for 3 hours. After cooling, the mixture is diluted with a 50% aqueous ammonia solution and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 2/1 heptane/ethyl acetate.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude product is purified by chromatography over silica gel
washwhile eluting with 2/1 heptane/ethyl acetate

Sources & evidence

ORD record: ord-fec0a556e0914b4a9d55a02aacb70ad4
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968581B2

Reaction notes

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