Water → 1-(4-Nitrobenzyl)-1H-1,2,4-triazole

HRID 487980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487980
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(OCC)(=O)C.O>CN(C=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 660114-Nitrobenzyl bromideHCID 454898221h-1,2,4-Triazole sodium salt

Produkt 1

HCID 64820001-(4-Nitrobenzyl)-1H-1,2,4-triazoleAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Nitrobenzylbromide (21.6 g, 0.1 mol) was added to a rapidly stirred suspension of 1,2,4-triazole sodium salt (9.1 g, 0.1 mol) in anhydrous DMF (100 ml) and the mixture stirred at room temperature for 16 h. Ethyl acetate (400 ml) was added followed by water (250 ml) and the layers separated. The organic phase was washed with water (3×250 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel eluting with ethyl acetate to give the title-product (10.6 g, 52%); m.p. 98°-100° C. δ (360 MHz, CDCl3) 5.47 (2H, s, CH2) 7.40 (2H, d, J=9 Hz, Ar-H), 8.02 (1H, s, Ar-H), 8.18 (1H, s, Ar-H), 8.23 (2H, d, J=9 Hz, Ar-H).

Aufarbeitung

  1. customthe layers separated
  2. washThe organic phase was washed with water (3×250 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3cef1c1583b6465a9e2fbe7978249b63
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298520

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