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Phenol → 3,5-Bis(4-hydroxyphenyl)-4-phenyl-1,2,4-triazole

HRID 5566
Notes
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Reaction equation

HRID 5566 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 996PhenolHCID 17424-Hydroxybenzoic acid hydrazideHCID 8870Benzenamine hydrochloride (1:1)HCID 87250Phenylparaben

Product 1

HCID 1360263553,5-Bis(4-hydroxyphenyl)-4-phenyl-1,2,4-triazoleYield 50%

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 began 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%. This monomer has the following structure: ##STR8##

Workup

  1. customwas removed via the distillation head
  2. temperaturethe temperature was increased to 250° C.
  3. waitheld for two hours
  4. temperatureThe mixture was cooled
  5. washwashed repeatedly in methanol

Sources & evidence

ORD record
ord-7b40b92986b142c0b4b761dffa4e4a2f
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05245043

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes