Acetic Acid → 4-(1H-benzimidazol-2-yl)phenol

HRID 986677노트

반응식

HRID 986677 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1([C:15](=N)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=[O:20])C>>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:15]1[C:9]1[CH:14]=[CH:13][C:12]([OH:20])=[CH:11][CH:10]=1

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 178513622HCID 178513622, 화합물

생성물 1

HCID 6756244-(1H-benzimidazol-2-yl)phenol수율 73%

실험 절차

A mixture of 324 g (0.3 mol) of o-phenylenediamine, 67.5 g (0.36 mol) of benzene carboximidoic acid, 4 hydroxy-, methyl ester hydrochloride and 450 ml of glacial acetic acid was stirred at reflux for two hours. After standing overnight at room temperature the hydrochloride salt of the benzimidazole was collected by filtration, washed with acetic acid, and finally ether. The hydrochloride salt of the product was suspended in 450 ml of dilute ammonium hydroxide, stirred for one hour at room temperature, and chilled briefly. The product was collected and the filter cake was treated with charcoal during recrystallization from a 2:1 water-alcohol mixture. Filtration gave 45.9 g (73%) of 4-(1H-benzimidazol-2-yl)phenol (mp 286°-289° C.) and a second crop of 2.8 g on standing.

후처리

  1. temperatureat reflux for two hours
  2. filtrationthe hydrochloride salt of the benzimidazole was collected by filtration
  3. washwashed with acetic acid, and finally ether
  4. stirringstirred for one hour at room temperature
  5. temperaturechilled briefly
  6. customThe product was collected
  7. additionthe filter cake was treated with charcoal during recrystallization from a 2:1 water-alcohol mixture
  8. filtrationFiltration

출처 및 근거

ORD 기록
ord-0bd6cdcbfc88413f8bae70a22b1ee41e
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04714762

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