Cesium carbonate → 1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

HRID 505513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505513
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[OH:11][C:12]1[C:20]2[N:19]=[N:18][NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:11])[C:20]=3[N:19]=[N:18]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 1650214-Methoxybenzyl bromideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 1363439141-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Methoxy-benzylbromide (2.976 g, 14.80 mmol) was added to a stirred suspension of 4-hydroxy-benztriazole (2.0 g, 14.80 mmol) and cesium carbonate (9.645 g, 29.6 mmol) in DMF (30 mL) at room temperature and the reaction mixture was stirred for 1 hour. Aqueous ammonium chloride (30 mL) was then added to quench the reaction and the mixture was then extracted with ethyl acetate (2×100 mL). The organic fractions were combined and concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2O, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2×100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to yield the title product. 1H NMR (DMSO d6) δ 10.67 (s, 1, H), 7.29-7.27 (m, 3H), 7.15 (d, J=8.3 Hz, 1H), 6.88-6.84 (m, 2H), 6.63 (d, J=7.6 Hz, 1H), 5.80 (s, 2H), 3.71 (s, 3H).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was then extracted with ethyl acetate (2×100 mL)
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with dichloromethane (2×100 mL)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b98674d0af74af7908ca3efe0d80d12
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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