2-Bromonaphthalene → 1-(4-Methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one

HRID 80039

반응식

HRID 80039 반응식
N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]1[CH2:26][CH2:25][NH:24][C:23]1=[O:27].Br[C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]1[CH2:26][CH2:25][N:24]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[C:23]1=[O:27]

참가 물질

9

반응물 4

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

생성물 1

HCID 498718661-(4-Methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one수율 73%

시약·촉매·용매 4

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

반응 조건

온도
110 °C

실험 절차

Copper iodide (21.5 mg, 0.113 mmol), trans-1,2-diamino cyclohexane (0.041 mL, 0.339 mmol) and potassium carbonate (313 mg, 2.26 mmol) were added to 1,4-Dioxane (15 mL) previously sparged with argon (10 minutes). The reaction mixture was sparged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 200 mg, 1.13 mmol) and 2-bromo naphthalene (234 mg, 1.13 mmol). The resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through a celite and the bed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent) afforded 250 mg (73% yield) of 1-(4-methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one.

후처리

  1. custompreviously sparged with argon (10 minutes)
  2. customThe reaction mixture was sparged with argon for a further 10 minutes
  3. temperatureThe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through a celite
  5. washthe bed was washed with chloroform
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent)

출처 및 근거

ORD 기록
ord-4c37a5aae42d4d56a69f1a90baaabf45
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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