Reaktion #10400

Reaktionsgleichung

2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid

tert-butyl carbazate

1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide

→

[2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester

Ausbeute 72.5%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated NaHCO3, water, and brine
2. 2
   TrocknenThe organic layer is dried over Na2SO4
3. 3
   Einengenconcentrated under vacuum
4. 4
   Sonstigepurified via column chromatography (1:3 ethyl acetate/hexanes)

Vorschrift

To a solution of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example 5, 2.18 g, 7.6 mmol) and tert-butyl carbazate (1.57 g, 11.8 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.25 g, 11.77 mmol). After stirring for 16 hours at room temperature, the reaction mixture is diluted with dichloromethane and then washed with saturated NaHCO3, water, and brine. The organic layer is dried over Na2SO4, concentrated under vacuum, and purified via column chromatography (1:3 ethyl acetate/hexanes) to afford [2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester as a solid (2.20 g). MS EI: m/z 400 (M+).

Quelle