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Toluene → 1,1'-(1,4-Phenylene)-bis[2-(4-hydroxyphenyl)benzimidazole]

HRID 1654969
Notes
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Reaction equation

HRID 1654969 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[CH:7][CH:6]=1.C1(O[C:30](=O)[C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)C=CC=CC=1.C1(S(C2C=CC=CC=2)(=O)=[O:46])C=CC=CC=1.[C:54]1([CH3:60])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[C:5]1([N:4]2[C:3]3[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=3[N:1]=[C:30]2[C:31]2[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=2)[CH:6]=[CH:7][C:8]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]=[C:60]2[C:54]2[CH:59]=[CH:58][C:57]([OH:46])=[CH:56][CH:55]=2)=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 1140TolueneHCID 31386Diphenyl sulfoneHCID 87250PhenylparabenHCID 225712721,4-Bis(2-aminoanilino)benzene

Product 1

HCID 1357047251,1'-(1,4-Phenylene)-bis[2-(4-hydroxyphenyl)benzimidazole]Yield 55%

Conditions

Temperature
150 °C

Procedure

A mixture of 1,4-bis(2-aminoanilino)benzene (28.73g, 0.099 mol), phenyl-4-hydroxybenzoate (42.96g, 0.201 mol), diphenylsulfone (126.45g), and toluene (100 ml) was heated under a nitrogen atmosphere for three hours at 150° C. The toluene was removed and the temperature increased to 290° C. and maintained for two hours. A vacuum was subsequently applied and maintained for one hour. The cooled purple reaction mixture was poured into warm toluene, and the solid recovered by filtration. The crude solid was washed in hot toluene and subsequently dried at 110° C. to afford a purple powder (44.2g, 90% crude yield), mp [Differential Scanning Calorimetry (DSC), heating rate of 10° C./min] sharp peak at 403° C. The solid was recrystallized twice from N,N-dimethylacetamide (DMAc) using charcoal to afford a white powder (26.95g, 55% yield). The compound exhibited a sharp melt by DSC (heating rate of 10° C./min) with a peak at 407° C. Anal. calcd. for (C 32 H22N4O2 : C, 77.72%; H, 4.48%; N, 11.33%; Found: C, 77.48%; H, 4.41%; N, 11.39%.

Workup

  1. customThe toluene was removed
  2. temperaturethe temperature increased to 290° C.
  3. temperaturemaintained for two hours
  4. temperaturemaintained for one hour
  5. additionThe cooled purple reaction mixture was poured
  6. temperatureinto warm toluene
  7. filtrationthe solid recovered by filtration
  8. washThe crude solid was washed in hot toluene
  9. customsubsequently dried at 110° C.
  10. customto afford
  11. temperaturea purple powder (44.2g, 90% crude yield), mp [Differential Scanning Calorimetry (DSC), heating rate of 10° C./min] sharp peak at 403° C
  12. customThe solid was recrystallized twice from N,N-dimethylacetamide (DMAc)

Sources & evidence

ORD record
ord-9aaf572ee93948f594d5b9bc1846260d
Source dataset
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05410012

Reaction notes

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