Sodium hydride → 2-(3-nitro-1H-pyrazol-1-yl)acetamide

HRID 546010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546010
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:12][C:13]([NH2:15])=[O:14]>CN(C)C=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:12][C:13]([NH2:15])=[O:14])[N:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 178526745HCID 178526745, Verbindung

Produkt 1

HCID 401765862-(3-nitro-1H-pyrazol-1-yl)acetamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 150 mg, 1.33 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (58 mg, 1.46 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 30 min, bromoacetamide (201 mg, 1.46 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2-(3-nitro-pyrazol-1-yl)-acetamide (107 mg, 48%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred for additional 30 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d95c2cabeeea49a28f0df0d50967addb
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935699B2

Notizen zur Reaktion

Wird geladen…