Acetic Acid → 1H-Benzimidazole, 2-propoxy-

HRID 397106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397106
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](O)(=O)C.[C:13]([O:16][CH2:17][CH3:18])(=O)C>C([O-])([O-])([O-])OCCC>[CH2:17]([O:16][C:13]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1)[CH2:18][CH3:9]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 8857Ethyl Acetate

Produkt 1

HCID 30406051H-Benzimidazole, 2-propoxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86586169Propyl orthocarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of o-phenylenediamine (2 g) in propyl orthocarbonate (5 ml) was added acetic acid (1.1 ml) and the solution was stirred at 80° C. for 3 hours. To the reaction mixture was added ethyl acetate, and the solution was washed with an aqueous solution of sodium hydrogen carbonate and water, then dried (Na2SO4), followed by concentration to dryness. The concentrate was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (1.54 g, 47%), m.p. 163-164° C.

Aufarbeitung

  1. washthe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  2. dry with materialdried (Na2SO4)
  3. concentrationfollowed by concentration to dryness
  4. customThe concentrate was purified by column chromatography on silica gel
  5. customto give crystals
  6. customRecrystallization from ethyl acetate-benzene afforded colorless crystals (1.54 g, 47%), m.p. 163-164° C.

Quellen und Nachweise

ORD-Eintrag
ord-b7b63f5abe6d4153b72b24ae16be65f1
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608210B2

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