1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one

HRID 2383723Notes

Reaction equation

HRID 2383723 reaction equation
N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29].Br[C:31]1[S:32][C:33]([CH3:36])=[CH:34][CH:35]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:24]1[CH2:28][CH2:27][N:26]([C:31]2[S:32][C:33]([CH3:36])=[CH:34][CH:35]=2)[C:25]1=[O:29]

Participants

9

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 698312-Bromo-5-methylthiopheneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498718671-(4-Methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-oneYield 74%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Copper iodide (16 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (28.8 mg, 0.25 mmol) and potassium phosphate (445 mg, 2.1 mmol) were added to 1,4-Dioxane (10 mL) previously degassed with argon (10 minutes). The reaction mixture was purged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.84 mmol) and 2-bromo-5-methylthiophene (150 mg, 0.84 mmol). The resulting mixture was heated to reflux at 110° C. for 4 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through celite and the celitebed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. The concentrate was quenched with ice, the precipitate formed was collected and dried to afford 170 mg (74% yield) of 1-(4-methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one.

Workup

  1. custompreviously degassed with argon (10 minutes)
  2. customThe reaction mixture was purged with argon for a further 10 minutes
  3. temperatureThe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe celitebed was washed with chloroform
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe concentrate was quenched with ice
  9. customthe precipitate formed
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-ba3620dd6cdf4294bc2260ba51b280a6
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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