m-Hydroxybenzohydrazide → 3-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenol
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
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
- temperatureThe reaction mixture was refluxed for 18 hours, during which time it
- additionpoured
- customThe aqueous solution was decanted
- customthe oily residue was purified by silica gel chromatography on Isco column
- customSolvent was removed in vacuo
Sources & evidence
- ORD record
- ord-00faf297fa924dfcac85aebf74044239
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652051B2
Reaction notes
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