Phenol → 3,5-Bis(4-hydroxyphenyl)-4-phenyl-1,2,4-triazole
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][CH:3]=1.C1(O[C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)C=CC=CC=1.C1(O)C=CC=CC=1.Cl.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:19]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 220 °C
Procedure
Into a 500 ml three neck round bottom flask equipped with a magnetic stirbar, nitrogen inlet, glass stopper, and distillation head was placed 4-hydroxybenzoic hydrazide (60.9 g, 0.4 mol) and phenyl-4-hydroxybenzoate (85.7 g, 0.4 mol). The mixture was heated to approximately 220° C. by use of a Wood's metal bath. The solids melt and phenol begins to evolve and was removed via the distillation head. After two hours, aniline hydrochloride (103.6 g, 0.8 mol) was added and the temperature was increased to 250° C. and held for two hours. The mixture was cooled and washed repeatedly in methanol to give a white solid (65.8 g, 50% yield). The solid was recrystallized from N,N-dimethylacetamide (approximately 225 ml) to give, after drying at 200° C. under vacuum, white needles (49.7 g, 37% yield) with a melting point of approximately 420° C. by differential thermal analysis (DTA). Elemental analysis for C20H15N3O2 : Calculated: C, 72.93%; H, 4.59%; N, 12.76%; O, 9.72%. Found: C, 72.97%; H, 4.63%; N, 12.84%.
Workup
- customwas removed via the distillation head
- temperaturethe temperature was increased to 250° C.
- waitheld for two hours
- temperatureThe mixture was cooled
- washwashed repeatedly in methanol
Sources & evidence
- ORD record
- ord-5b1a1406b9504be4919719853f7565fc
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05182356
Reaction notes
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