m-Hydroxybenzohydrazide → 3-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenol

HRID 387453

Reaktionsgleichung

Reaktionsgleichung von HRID 387453
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=O.I.CS[C:15](=[NH:28])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=1>N1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:15]2[NH:28][C:5]([C:4]3[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10][CH:9]=3)=[N:7][N:8]=2)=[CH:18][C:19]=1[C:24]([F:25])([F:26])[F:27]

Komponenten

4

Edukt 2

HCID 79889m-HydroxybenzohydrazideHCID 1785040011-[4-chloro-3-(trifluoromethyl)phenyl]-S-methylisothiourea hydroiodide

Produkt 1

HCID 1785159893-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenolAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-hydroxybenzoic acid hydrazide (2.98 g, 19.58 mmol) and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl]isothiourea hydroiodide (7.78 g, 19.63 mmol) were suspended in 40 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours, during which time it changed color from yellow into dark-red. Then it was cooled down to ambient temperature and poured with stirring into 250 mL of ice-water. The aqueous solution was decanted and the oily residue was purified by silica gel chromatography on Isco column using 0=>50% gradient of ethyl acetate in hexane. Solvent was removed in vacuo to give the title product as a white solid (2.176 g). 31.3% yield.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 hours, during which time it
  2. additionpoured
  3. customThe aqueous solution was decanted
  4. customthe oily residue was purified by silica gel chromatography on Isco column
  5. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-854ec41e5fb84ca4ae891ea9a3bcaa1f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372971B2

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