Reaktion #623240

Reaktionsgleichung

HCl

methylamine hydrochloride

2-fluoro-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonyl chloride

triethylamine

→

2-fluoro-N-methyl-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide

Ausbeute 72.0%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to room temperature
2. 2
   Extraktionextracted with EtOAc
3. 3
   ExtraktionThe organic extract
4. 4
   Trocknenwas dried (Na2SO4)
5. 5
   Einengenconcentrated

Vorschrift

A mixture of 2-fluoro-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonyl chloride (15 g, crude) in THF (150 mL) at −45° C. was treated with methylamine hydrochloride (5.96 g, 89 mmol) and then treated dropwise with triethylamine (12.4 mL, 89 mmol). After stirring for 1 hour at −45° C., the mixture was adjusted to pH 3 by the addition of aqueous 3M HCl, warmed to room temperature, diluted with water, and extracted with EtOAc. The organic extract was dried (Na2SO4), concentrated, and subjected to flash chromatography (9-17% EtOAc-petroleum ether) to give 2-fluoro-N-methyl-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (10 g, 72% for two steps) as a yellow solid. MS (m/z) 333.0 (M+H+).

Quelle