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

HRID 2427135
Notes
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Reaction equation

HRID 2427135 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 223378254-Bromo-2-(trifluoromethyl)benzonitrileHCID 671312104-(4-Fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidine-2,5-dione

Product 1

HCID 671310494-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalyst
HCID 222
Ammonia
Solvent
HCID 31374DimethylacetamideSolvent

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

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography over silica gel
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes