StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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

HRID 80040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80040
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9d155cf1125b484f9d5ab50ed4b67e28
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE045173E1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion