Sodium Hydroxide → (E)-4-methyl-2-styryl-1H-benzimidazole

HRID 382548

Reaktionsgleichung

Reaktionsgleichung von HRID 382548
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[C:10](O)(=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH3:9][C:3]1[C:2]2[N:1]=[C:10](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 175932,3-DiaminotolueneHCID 444539Cinnamic Acid

Produkt 1

HCID 22736633(E)-4-methyl-2-styryl-1H-benzimidazoleAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 2,3-diaminotoluene (2.44 g, 20 mmol), (E)-cinnamic acid (2.96 g, 20 mmol) and polyphosphoric acid (10 g) was heated to 180° C. for 90 min. The hot mixture was poured into water (100 ml), basified with 50% aqueous solution of sodium hydroxide and extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (100 ml) and brine (100 ml), dried (magnesium sulfate) and concentrated to dryness. Purification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3)) yielded 0.61 g (13%) of the titled compound as red solids.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×100 ml)
  2. washThe combined extracts were washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated to dryness
  5. customPurification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3))

Quellen und Nachweise

ORD-Eintrag
ord-c5fd9300e7a34cb499021e518bfba359
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310079B1

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