Reaktionsgleichung
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].Cl.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1)#[N:13].N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C.Cl>[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)=[CH:16][CH:15]=1)#[N:13]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
An aliquot of 3-iodobenzoyl chloride (1.1 g, 4.2 mmol) was taken up in tetrahydrofuran (“THF”, 25 mL), and cooled to approximately 0° C. in an ice-water bath. To the cold solution were added 4-cyanobenzylamine hydrochloride (0.71 g, 4.2 mmol) and pyridine (0.66 g, 8.3 mmol). The solution gradually warmed to room temperature, and was stirred for 72 hours. The reaction mixture was diluted with ethyl acetate (25 mL) and aqueous HCl (25 mL). The organic phase was separated, dried (MgSO4), filtered, and rotary evaporated. The resulting crude product was purified using silica gel chromatography (elution with dichloromethane/THF [9:1]) to give N-(4-cyano-benzyl)-3-iodo-benzamide (0.76 g, 51%) as a white solid. 1H-NMR (DMSO-d6) δ 9.2 (t, 1H), 8.2 (s, 1H), 7.9 (m, 2H), 7.8 (d, 2H), 7.5 (d, 2H), 7.3 (m, 1H), 4.5 (d, 2H) ppm.
Aufarbeitung
- temperatureThe solution gradually warmed to room temperature
- customThe organic phase was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe resulting crude product was purified
- washsilica gel chromatography (elution with dichloromethane/THF [9:1])
Quellen und Nachweise
- ORD-Eintrag
- ord-65daf1c7ed2e423e80a6a7402d8e3650
- Quelldatensatz
- uspto-grants-2005_02
- Patentnummer
- US06849648B2
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