3-Bromotoluene → 1-(4-Methyl-pyridin-3-yl)-3-m-tolyl-imidazolidin-2-one

HRID 80080

Reaktionsgleichung

Reaktionsgleichung von HRID 80080
[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]([CH3:21])[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:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:13]

Komponenten

7

Edukt 4

HCID 115603-BromotolueneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 498720561-(4-Methyl-pyridin-3-yl)-3-m-tolyl-imidazolidin-2-oneAusbeute 67,69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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-methyl-benzene (172.8 mg, 1.017 mmol), 1,4-dioxane (20 mL), copper iodide (16.13 mg, 0.0847 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.254 mmol) and potassium phosphate (539.3 mg, 2.541 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.2% MeOH in CHCl3) afforded 153 mg of the product (67.69% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-081a6f9ce45444b9992466e14b9e6f7f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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