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

HRID 80040

반응식

HRID 80040 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 887Methanol용매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9d155cf1125b484f9d5ab50ed4b67e28
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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