Triethylamine → 2-Pentyl-1H-benzimidazole

HRID 1655447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655447
[2H][C:2]1[C:7]([2H])=[C:6]([NH2:9])[C:5]([NH2:10])=[C:4]([2H])[C:3]=1[2H].C(N(CC)CC)C.[C:20](Cl)(=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(Cl)Cl>[CH2:21]([C:20]1[NH:9][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[N:10]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 107729501,2-Diaminobenzene (D4, 98%)

Produkt 1

HCID 221232-Pentyl-1H-benzimidazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of O-phenylenediamine (2.2 g) and triethylamine (2.0 g) in methylene chloride (20 ml) was added dropwise caproyl chloride (2.3 g) with stirring under ice-cooling. The mixture was stirred for 3 hours at room temperature, washed with a saturated aqueous sodium bicarbonate and water, then dried. The solvent was evaporated. To the residue was added 3N-HCl, and the mixture was heated for 1.5 hour under reflux. The reaction mixture was made basic with 6N NaOH. Then precipitating crystals were recrystallized from ethyl acetate-hexane to give colorless needles (1.5 g, 47%), m.p. 161-162° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. washwashed with a saturated aqueous sodium bicarbonate and water
  4. customdried
  5. customThe solvent was evaporated
  6. additionTo the residue was added 3N-HCl
  7. temperaturethe mixture was heated for 1.5 hour
  8. temperatureunder reflux
  9. customThen precipitating crystals
  10. customwere recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6cc51fa1d32a4b1b92a1f056fc905f0c
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250554

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