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

HRID 661408Notes

Reaction equation

HRID 661408 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 1785159893-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenolYield 31.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc3edaf0b1bd4f018bf30a6ff48b717d
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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