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

HRID 1654969
ノート
印刷プレビュー

反応式

HRID 1654969 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
150 °C

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-9aaf572ee93948f594d5b9bc1846260d
出典データセット
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05410012

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート