Potassium Carbonate → 1-Benzothiazol-2-yl-3-(4-methylpyridin-3-yl)imidazolidin-2-one

HRID 80073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80073
[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[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[N:10]1[CH2:11][CH2:12][N:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:9]1=[O:13]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 6120402-Bromo-1,3-benzothiazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 687822331-Benzothiazol-2-yl-3-(4-methylpyridin-3-yl)imidazolidin-2-oneAusbeute 36,5 %

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, 0.84 mmol) was reacted with 2-bromo-benzothiazole (179 mg, 0.847 mmol), 1,4-dioxane (10 mL), copper iodide (16 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (28.8 mg, 0.25 mmol) and potassium carbonate (231 mg, 1.68 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% MeOH in CHCl3) afforded 95 mg of the product (36.5% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-a4f49fdd26e641c298ba40c00949a3cc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

Notizen zur Reaktion

Wird geladen…