Pyridine → Ethyl 2-(2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)-3-dimethylaminoacrylate

HRID 1861213

Reaktionsgleichung

[CH3:1][N:2]([CH3:10])[CH:3]=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].N1C=CC=CC=1.[F:17][C:18]1[C:26]([CH3:27])=[C:25]([F:28])[C:24]([F:29])=[C:23]([N+:30]([O-:32])=[O:31])[C:19]=1[C:20](Cl)=[O:21]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:10])[CH:3]=[C:4]([C:20](=[O:21])[C:19]1[C:23]([N+:30]([O-:32])=[O:31])=[C:24]([F:29])[C:25]([F:28])=[C:26]([CH3:27])[C:18]=1[F:17])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

1.4 g (0.01 mol) of ethyl 3-dimethylaminoacrylate, 15 mg of ethyl acetate and 0.8 mg (0.01 mol) of pyridine were loaded and cooled below 5° C., and a liquid mixture of 3 g (0.01 mol) of 2,4,5-trifluoro-3-methyl-6-nitrobenzoyl chloride and 5 ml of ethyl acetate was added dropwise while the temperature was maintained at 0 to 5° C. The resulting mixture was stirred at 5° C. for 1 hour and then stirred at room temperature (25° C.) overnight (12 hours). The precipitated pyridine hydrochloride was filtered off, and the filtrate was concentrated under reduced pressure to give 3.62 g of ethyl 3-dimethylamino-2-(2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)acrylate with a 87% purity (in terms of the percentage of the peak area in HPLC) as the residue.

Aufarbeitung

temperaturecooled below 5° C.
additionwas added dropwise while the temperature
stirringstirred at room temperature (25° C.) overnight (12 hours)
filtrationThe precipitated pyridine hydrochloride was filtered off
concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-d6e6b984bd674c68a064086fea3d5f04
Quelldatensatz: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06531624B1

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