4-[(Methoxymethoxy)methyl]-2-nitro-3-thiophenesulfonamide → 2-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

Participants

Reaction Steps

4-[(Methoxymethoxy)methyl]-2-nitrothiophene-3-sulfonamide (1.8 g, 6.4 mmol) was reacted with iron powder (1.43 g, 4 equivalents) in acetic acid (70 mL) at 50° C. for 7.5 hours then concentrated under reduced pressure. A slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g) and further rinsed with 5% methanol/dichloromethane (300 mL). The filtrate was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel using a Biotage-12s column eluting with 2.5:97.5 methanol: dichloromethane to give 2-amino-4-[(methoxymethoxy)methyl]thiophene-3-sulfonamide (1 g, 62%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.30 (s, 3 H), 4.53 (s, 2 H), 4.66 (s, 2 H), 6.28 (s, 1 H), 6.61 (s, 2 H), 6.94 (s, 2 H).

Provenance & Evidence