2-Bromopyridine → 1-(Pyridin-2-yl)imidazolidin-2-one

HRID 1442877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442877
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.CC([O-])=O.[K+]>N1C=CC=CC=1.[Cu].Cl[Cu]>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Komponenten

7

Edukt 3

HCID 79732-BromopyridineHCID 84532-ImidazolidinoneHCID 517044Potassium Acetate

Produkt 1

HCID 2942411-(Pyridin-2-yl)imidazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 62652Cuprous chlorideKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-imidazolidinone (1.00 g, 11.6 mmol), 2-bromopyridine (3.40 mL, 34.8 mmol), copper powder (2.58 g, 40.7 mmol), CuCl (230 mg, 2.32 mmol), and KOAc (3.99 g, 40.7 mmol) in pyridine (10 mL) was heated at 60° C. for 18 h. The cooled mixture was partitioned between CHCl3 (100 mL) and 10% aqueous citric acid (50 mL). The aqueous layer was adjusted to pH 11 with 10 N aqueous NaOH, extracted with CHCl3 (3×100 mL), and these organic layers were combined and dried over Na2SO4, filtered, and concentrated under reduced pressure, to give the title compound in sufficient purity for use in the next step. MS: m/z=164 (M+1).

Aufarbeitung

  1. customThe cooled mixture was partitioned between CHCl3 (100 mL) and 10% aqueous citric acid (50 mL)
  2. extractionextracted with CHCl3 (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5619a3604ca0456fa99ac7aa39994fad
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659300B2

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