Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[CH:44]=[CH:43][C:27]([CH2:28][CH2:29][NH:30][C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35](Cl)=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[CH:26][CH:25]=1>CS(C)=O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH2:29][NH:30][C:31]([C:32]2[CH:37]=[CH:36][C:35]([O:12][C:11]3[CH:10]=[C:9]4[C:4]([CH:5]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:7][O:8]4)=[CH:3][C:2]=3[Cl:1])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[O:42])=[CH:43][CH:44]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 62 °C
Versuchsvorschrift
Methyl 6-chloro-7-hydroxychroman-4-carboxylate (100 mg, 0.412 mmol) (Preparation 4, substituting methanol for ethanol in Step C) was diluted with DMSO (1 mL) followed by the addition of K2CO3 (68.3 mg, 0.495 mmol) and N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamide (140 mg, 0.412 mmol). The reaction was heated to 62° C. and stirred for 3 hours. The reaction was cooled, loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate (60 mg, 26.7% yield).
Aufarbeitung
- temperatureThe reaction was cooled
- washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-ae5673de7aac404c85f0a9daf7a4d920
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08716498B2
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