4-[(Methoxymethoxy)methyl]-2-nitro-3-thiophenesulfonamide → 2-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide
Reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[C:7]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:8]([N+:11]([O-])=O)[S:9][CH:10]=1>C(O)(=O)C.[Fe]>[NH2:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[C:7]=1[S:14]([NH2:17])(=[O:15])=[O:16]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- concentrationthen concentrated under reduced pressure
- filtrationA slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g)
- washfurther rinsed with 5% methanol/dichloromethane (300 mL)
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue purified by flash chromatography on silica gel using a Biotage-12s column
- washeluting with 2.5:97.5 methanol
Sources & evidence
- ORD record
- ord-f96b41158a80427aadb3eb8a5f6ce7f1
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951800B2
Reaction notes
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