2,6-Dibromotoluene → 1-Benzyl-3-(3-bromo-2-methylphenyl)imidazolidin-2-one

HRID 1811046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811046
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[CH2:10]([N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH2:10]([N:17]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=2[CH3:9])[C:18]1=[O:22])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 346812,6-DibromotolueneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 2314031-Benzylimidazolidin-2-one

Produkt 1

HCID 593750871-Benzyl-3-(3-bromo-2-methylphenyl)imidazolidin-2-oneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Step 2 A mixture of 1,3-dibromo-2-methylbenzene (0.147 mL, 1.064 mmol), 1-benzylimidazolidin-2-one (75 mg, 0.426 mmol), copper (I) iodide (8.11 mg, 0.043 mmol), (+/−)-trans-1,2-diaminocyclohexane (5.1 mL, 0.043 mmol) and tripotassium phosphate (181 mg, 0.851 mmol) in dioxane (2 mL) was sonicated while bubbling with argon for 1 min. The mixture was heated in a sealed tube at 120° C. After 18.25 h, the mixture was cooled to rt, diluted with EtOAc and filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 20:80 EtOAc-hexane to EtOAc) to provide 1-benzyl-3-(3-bromo-2-methylphenyl)imidazolidin-2-one as a waxy white solid (36 mg, 25%). 1H NMR (400 MHz, chloroform-d) δ 7.49 (1 H, dd, J=7.9, 0.9 Hz), 7.28-7.40 (5 H, m), 7.19 (1 H, dd, J=7.8, 1.0 Hz), 7.08 (1 H, t, J=7.9 Hz), 4.46 (2 H, s), 3.64 (2 H, dd, J=8.8, 6.8 Hz), 3.37 (2 H, dd, J=8.8, 7.0 Hz), 2.36 (3 H, s). Mass spectrum m/z 346.8 (M+H)+.

Aufarbeitung

  1. customwas sonicated
  2. customwhile bubbling with argon for 1 min
  3. temperaturethe mixture was cooled to rt
  4. additiondiluted with EtOAc
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography (
  8. washeluting with a gradient from 20:80 EtOAc-hexane to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c459b6ca4fe74b8ab34be123fad94ffa
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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