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
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of the product of Example 10D (1.8 g, 6.4 mmol) in acetic acid (70 mL) was treated with iron powder (1.43 g, 25.5 mmol), stirred at 50° C. for 7.5 h and concentrated. A mixture of the residue in 5% methanol in dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g), and rinsed with 5% methanol in dichloromethane (300 mL). The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel, eluting with methanol in dichloromethane to give the title compound (1 g, 62%). 1H NMR (300 MHz, DMSO-d6): δ 6.94 (s, 2 H), 6.61 (s, 2 H), 6.28 (s, 1 H), 4.66 (s, 2 H), 4.53 (s, 2 H), 3.30 (s, 3 H).
Workup
- concentrationconcentrated
- additionA mixture of the residue in 5% methanol in dichloromethane (60 mL)
- filtrationwater (6 mL) was filtered through silica gel (20 g)
- washrinsed with 5% methanol in dichloromethane (300 mL)
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was chromatographed on silica gel
- washeluting with methanol in dichloromethane
Sources & evidence
- ORD record
- ord-ddd66ac5223c4ff697e3cb7098c32d74
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538105B2
Reaction notes
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