Benzene, 1-bromo-3-(trifluoromethyl)- → 1-(4-Methyl-pyridin-3-yl)-3-(3-trifluoromethyl-phenyl)-imidazolidin-2-One

HRID 2383781Notes

Reaction equation

HRID 2383781 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498721501-(4-Methyl-pyridin-3-yl)-3-(3-trifluoromethyl-phenyl)-imidazolidin-2-OneYield 70.11%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.847 mmol) was reacted with 1-bromo-3-trifluoromethyl-benzene (0.14 mL, 1.016 mmol), 1,4-dioxane (10 mL), copper iodide (16.13 mg, 0.0847 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.254 mmol) and potassium phosphate (539 mg, 2.54 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.2% MeOH in CHCl3) afforded 190 mg of the product (70.11% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-3b42d2e53ae747158b69c9836166c364
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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