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

HRID 1913699

Reaktionsgleichung

[I:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.[NH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[OH:33]>N1C=CC=CC=1>[OH:33][C:24]1[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[CH:28][C:23]=1[NH:22][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[I:1]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 1.78 g of 3-iodo-isonicotinic acid, 1.38 g of WSC and 12 ml of pyridine was stirred while heating at 50° C. for 15 minutes. Then, 1.15 g of 2-amino-4-(trifluoromethyl)phenol was added to the reaction mixture. The reaction mixture was stirred while heating at 80° C. for two hours. The reaction mixture was returned to room temperature, and concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 1.81 g of N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3iodo isonicotinamide.

Aufarbeitung

stirringThe reaction mixture was stirred
temperaturewhile heating at 80° C. for two hours
customwas returned to room temperature
concentrationconcentrated under reduced pressure
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

Quellen und Nachweise

ORD-Eintrag: ord-b5c50467b3414a24b1e17740877d3a23
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609705B2

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