Benzaldehyde → HCID 178418547, Verbindung

HRID 4718

Reaktionsgleichung

Reaktionsgleichung von HRID 4718
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[K+].[Br-]>CCOCC>[Cl-:9].[C:16]([O:8][CH:1]([N+:13]1[CH:14]=[CH:15][N:11]([CH3:10])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 13901-MethylimidazoleHCID 7412Benzoyl chlorideHCID 253877Potassium Bromide

Produkt 1

HCID 178418547HCID 178418547, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To an ether solution of benzoyl chloride 2.81 g (0.02 mol) there was added dropwise 1.67 g (0.02 mol) 1-methylimidazole with stirring. The resulting mixture was evaporated in vacuo and the residue was allowed to react with 2.12 g (0.02 mol) benzaldehyde at 70° overnite. After cooling, the reaction mixture was triturated with ether and was solid separated by filtration. Recrystallization from dichloromethane:dioxane gave 4.2 g (0.012 mol), 65%, 9, mp 199°-201°; ir (KBr) 1740 cm-1 ; pmr (CDCl3) δ 4.17 (s, 3H), 8.18-7.25 (m, 12H), 8.50 (s, 1H) and 11.1 (bs, 1H) ppm.

Aufarbeitung

  1. customThe resulting mixture was evaporated in vacuo
  2. temperatureAfter cooling
  3. customthe reaction mixture was triturated with ether
  4. customseparated by filtration
  5. customRecrystallization from dichloromethane
  6. customdioxane gave 4.2 g (0.012 mol), 65%, 9, mp 199°-201°

Quellen und Nachweise

ORD-Eintrag
ord-61f54da028b24a72bc1f764a9ad4f9e4
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727151

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