Ethyl Acetate → 4-Methyl-5-nitro-2-(1,2,4-triazol-1-yl)pyridine

HRID 2393432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393432
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C(OCC)(=O)C>CN(C=O)C.O>[CH3:19][C:17]1[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=[C:13]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:18]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Produkt 1

HCID 542579534-Methyl-5-nitro-2-(1,2,4-triazol-1-yl)pyridineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1,2,4-triazole (4.0 g, 58 mmol) in dry DMF (20 mL) was added potassium carbonate (12.0 g, 87 mmol) and 2-chloro-4-methyl-5-nitropyridine (10 g, 58 mmol) and the mixture stirred at ambient temperature under nitrogen for 24 hours. Ethyl acetate (500 mL) and water (250 mL) were added to the mixture and the resulting precipitate was collected by filtration to give the title compound (5.08 g, 43%) as a pale brown solid. The filtrate was separated and the organic phase was washed with water (250 mL) and brine (250 mL), dried (MgSO4) and evaporated. The residue was triturated with ethyl acetate and the precipitate collected by filtration to give the title compound as a brown solid (4.11 g, 35%, overall yield 78%). mp 198°-200° C. 1H NMR (360 MHz, CDCl3) δ 2.72 (3H, s), 7.86 (1H, s), 8.07 (1H, s), 9.03 (1H, s) and 9.15 (1H, s).

Aufarbeitung

  1. filtrationthe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c3c48edb37544b628d29edb48a16cb8f
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807857

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