Triethylamine → 3-Bromo N (2 (2 (2 methoxyethoxy)ethoxy)ethyl)-5-nitrobenzamide
Reaktionsgleichung
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=1)[C:23]([OH:25])=O.[CH3:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH2:42].CCN(CC)CC>CCOC(C)=O>[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=1)[C:23]([NH:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH3:32])=[O:25]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
T3P, 50 wt % in EtOAc (25 mL, 42.0 mmol) was slowly added to a solution of 3-bromo-5-nitrobenzoic acid (7.05 g, 28.7 mmol), 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (4 g, 24.25 mmol) and Et3N (12 mL, 86 mmol) in EtOAc (50 mL) whilst immersed in an ice-bath. Once the addition was complete, the ice bath was removed and the reaction allowed to stir at rt for 2 h. The mixture was partitioned between sat. aq. NaHCO3 solution (100 mL) and EtOAc (100 mL). The organic layer was washed with aq K2CO3 solution (10 g in 100 mL) and brine (100 mL), before being dried (MgSO4), filtered and concentrated in vacuo to afford the sub-title compound (8.23 g) as a brown oil.
Aufarbeitung
- customimmersed in an ice-bath
- additionOnce the addition
- customthe ice bath was removed
- customThe mixture was partitioned between sat. aq. NaHCO3 solution (100 mL) and EtOAc (100 mL)
- washThe organic layer was washed with aq K2CO3 solution (10 g in 100 mL) and brine (100 mL)
- dry with materialbefore being dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-af27732daae04bc2956f569f8b468cef
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08927563B2
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