Reacción #917

Ecuación de reacción

water

sodium acetate

methoxyamine hydrochloride

N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide

→

title compound

Rendimiento 96.2%

N-(1,1-Dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide

Rendimiento 96.2%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   TemperaturaThe white suspension was heated at
3. 3
   Temperaturaa gentle reflux overnight ca. 16 hours
4. 4
   ExtracciónThe aqueous mixture was extracted with four 100 mL portions of methylene chloride
5. 5
   LavadoThe combined extracts were washed with water
6. 6
   Secadodried (MgSO4)
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

To a suspension of 3.91 g (46.8 mmol) of methoxyamine hydrochloride in 60 mL of methanol was added 3.84 g (46.8 mmol) of sodium acetate. After stirring the white suspension for ca. 15 minutes 5.72 g (23 mmol) of N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide was added in one portion. The white suspension was heated at a gentle reflux overnight ca. 16 hours. The reaction mixture was cooled to room temperature and poured into 500 mL of water. The aqueous mixture was extracted with four 100 mL portions of methylene chloride. The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo yielding 5.74 g of the title compound as a white solid, m.p. 99°-101° C.

Fuente