Sodium Iodide → 1-(4-chlorobenzyl)-5-(4-methoxybenzyloxy)pyridine-2(1H)-one

HRID 1948276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948276
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:5][N:4]=1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.[Na+].[I-]>C(#N)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:4]2[CH:5]=[C:6]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:7]=[CH:8][C:3]2=[O:2])=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 693450322-Methoxy-5-(4-methoxybenzyloxy)pyridine

Produkt 1

HCID 589669521-(4-chlorobenzyl)-5-(4-methoxybenzyloxy)pyridine-2(1H)-oneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

According to Scheme 32 Step 1: 2-Methoxy-5-(4-methoxybenzyloxy)pyridine (1.38 mmol, 339 mg), 4-chlorobenzylchloride (2.76 mmol, 468 mg), NaI (1.38 mmol, 207 mg) in acetonitrile (15 mL) was heated at 150° C. for 50 minutes under microwave conditions. The cooled crude reaction washed with water, extracted with AcOEt. The organic layer was collected, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge CH2Cl2 and CH2Cl2/acetone 90/10) yielding 1-(4-chlorobenzyl)-5-(4-methoxybenzyloxy)pyridine-2(1H)-one (141 mg, 29%).

Aufarbeitung

  1. temperatureThe cooled crude
  2. customreaction
  3. washwashed with water
  4. extractionextracted with AcOEt
  5. customThe organic layer was collected
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified in a manifold (vac.)

Quellen und Nachweise

ORD-Eintrag
ord-574aba88b9924a97b344729d297439a2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399493B2

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