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Acetic Acid → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-7-carboxylate

HRID 1977371
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HRID 1977371 반응식
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:33]([O-])([O-])([O-])[O:34][CH3:35]>>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:7]3[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=[CH:16][C:6]=3[N:5]=[C:33]2[O:34][CH3:35])=[CH:20][CH:21]=1)#[N:32]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 19872204Methyl orthocarbonate

생성물 1

HCID 22596778Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-7-carboxylate

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온도
80 °C

실험 절차

Acetic acid (0.2 g) was added to a solution of ethyl 3-amino-2-[(2′-cyanobiphenyl-4-yl)methyl]aminobenzoate (1.1 g) in methyl orthocarbonate (5 ml). The mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated, and the concentrate was extracted with ethyl acetate. The organic layer was then washed with an aqueous solution of sodium hydrogen carbonate and water. The solvent was evaporated in vacuo to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (1.09 g, 90%), m.p. 160-161° C.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe concentrate was extracted with ethyl acetate
  3. washThe organic layer was then washed with an aqueous solution of sodium hydrogen carbonate and water
  4. customThe solvent was evaporated in vacuo
  5. customto give crystals
  6. customRecrystallization from ethyl acetate-benzene afforded colorless crystals (1.09 g, 90%), m.p. 160-161° C.

출처 및 근거

ORD 기록
ord-5c2bdfd0289440b18e875b673b105f88
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06232334B1

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