Reaktion #2346367

Reaktionsgleichung

water

sodium acetate

methoxyamine hydrochloride

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

→

title compound

Ausbeute 96.2%

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

Ausbeute 96.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   TemperaturThe white suspension was heated at
3. 3
   Temperatura gentle reflux overnight ca. 16 hours
4. 4
   ExtraktionThe aqueous mixture was extracted with four 100 mL portions of methylene chloride
5. 5
   WaschenThe combined extracts were washed with water
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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. 1H NMR (CDCl3, 200 MHz.) δ: 8.51(s,1H), 6.66(d,1H), 6.54(d,1H), 4.82(bs,1H), 3.97(s,3H), 3.82(s,3H), 1.24(s, 9H).

Quelle