Acetic Anhydride → 7-[N-acetyl-N-(4-Chlorophenyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[N:16]([CH3:18])[C:15](=[O:19])[N:14]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[C:17]3[N:16]([CH3:18])[C:15](=[O:19])[N:14]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)[C:29](=[O:31])[CH3:30])=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A mixture of 4-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.393 g, 1.0 mmol), pyridine (0.1 ml) and acetic anhydride (10 ml) was heated at 120° C. for 4 days. The mixture was evaporated in vacuo. The residue was diluted with ethyl acetate (50 ml), washed with saturated sodium bicarbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed eluting with 40-50% ethyl acetate/hexanes to give N-(4-chlorophenyl)-N-[1-(4-methoxybenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-4-yl]acetamide (0.388 g, quant.) as an oil.
Aufarbeitung
- customThe mixture was evaporated in vacuo
- additionThe residue was diluted with ethyl acetate (50 ml)
- washwashed with saturated sodium bicarbonate
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customchromatographed
- washeluting with 40-50% ethyl acetate/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-38709787dc564bdfbbd06675dbae8d03
- Quelldatensatz
- uspto-grants-2010_05
- Patentnummer
- US07714009B2
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