Toluene → 5,5'-Oxy-bis[2-(4-hydroxyphenyl)benzimidazole]

HRID 5567Notes

Reaction equation

HRID 5567 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH2:17])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C1(O[C:25](=O)[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)C=CC=CC=1.C1(S(C2C=CC=CC=2)(=O)=[O:41])C=CC=CC=1.[C:49]1([CH3:55])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>>[O:9]([C:10]1[CH:15]=[CH:14][C:13]2[N:16]=[C:25]([C:26]3[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=3)[NH:17][C:12]=2[CH:11]=1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]=[C:55]([C:49]3[CH:54]=[CH:53][C:52]([OH:41])=[CH:51][CH:50]=3)[NH:1][C:2]=2[CH:3]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 31386Diphenyl sulfoneHCID 758873,3',4,4'-Tetraaminodiphenyl etherHCID 87250Phenylparaben

Product 1

HCID 1360291415,5'-Oxy-bis[2-(4-hydroxyphenyl)benzimidazole]Yield 30%

Conditions

Temperature
150 °C

Procedure

A mixture of bis(3,4-diaminophenyl)ether (22.00 g, 0.096 mol), phenyl-4-hydroxybenzoate (41.00 g, 0.194 mol), diphenylsulfone (110.17 g), and toluene (135 ml) was heated under a nitrogen atmosphere for 3.5 hours at 150° C. The toluene was removed and the temperature increased to 250° C. and maintained for 1.5 hours. A vacuum was subsequently applied and the temperature increased to 280° C. and maintained for 1.25 hours. The cooled dark reaction mixture was washed in hot toluene and dried at 110° C. to afford 20.59 g (50% crude yield) of a dark purple powder. The dark solid was extracted with acetone to afford 12.39 g (30% yield) of a tan solid. The endothermic peak as determined by DTA was 317° C. (broad). Analysis calcd. for C26H18N4O3 : C, 71.88%; H, 4.18%; N, 12.90%. Found: C, 71.91%; H, 4.22%; N, 13.06%. The resulting monomer had the following structural formula: ##STR11##

Workup

  1. customThe toluene was removed
  2. temperaturethe temperature increased to 250° C.
  3. temperaturemaintained for 1.5 hours
  4. temperaturethe temperature increased to 280° C.
  5. temperaturemaintained for 1.25 hours
  6. customThe cooled dark reaction mixture
  7. washwas washed in hot toluene
  8. customdried at 110° C.
  9. customto afford 20.59 g (50% crude yield) of a dark purple powder
  10. extractionThe dark solid was extracted with acetone

Sources & evidence

ORD record
ord-067a37df0148453b970f7e876cfd2a25
Source dataset
uspto-grants-1993_09
Patent number
US05245044

Reaction notes

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