Réaction #917

Équation de réaction

water

sodium acetate

methoxyamine hydrochloride

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

→

title compound

Rendement 96.2%

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

Rendement 96.2%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   TempératureThe white suspension was heated at
3. 3
   Températurea gentle reflux overnight ca. 16 hours
4. 4
   ExtractionThe aqueous mixture was extracted with four 100 mL portions of methylene chloride
5. 5
   LavageThe combined extracts were washed with water
6. 6
   Séchagedried (MgSO4)
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source