1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

HRID 1913697

Reaktionsgleichung

[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[OH:22])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 0.69 g of 3-bromo isonicotinic acid, 0.60 g of 2-amino-4-(trifluoromethyl)phenol, 1.00 g of WSC and 6 ml of pyridine was stirred while heating at 80° C. for two hours. The reaction mixture was cooled to room temperature, and then concentrated. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixture solvent of ethyl acetate and hexane to give 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
additionWater was added to the residue
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
washThe residue was washed with a mixture solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag: ord-942da88e0d284fdaa568ed4c1ad1226b
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609705B2

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