1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23000173, Verbindung

HRID 398350

Reaktionsgleichung

Reaktionsgleichung von HRID 398350
O[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1)=[N+:27]=[N-:28]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 135055565-(Hydroxymethyl)-1H-benzimidazole

Produkt 1

HCID 23000173HCID 23000173, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) suspension of 5-(hydroxymethyl)-benzimidazole (920 mg, 6.2 mmol) in THF (12 mL) was added sequentially DPPA (1.46 mL, 6.8 mmol) and DBU (1.11 mL, 7.4 mmol). The resulting solution was heated to reflux for 5 h, cooled to RT, and concentrated in vacuo. The residue was partitioned between sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. Silica gel chromatography (15% MeOH—CHCl3), afforded the title compound as a brown solid:

Aufarbeitung

  1. temperatureTo a cooled
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between sodium bicarbonate and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8af5f06729a4bdfa7640ff663c00ac4
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610692B1

Verknüpfte Notizen

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