Acetic Acid → N-{3-[(Propan-2-ylsulfonyl)methyl]phenyl}acetamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:5]=1)([O-])=O.O.C(Cl)Cl.[C:21](O)(=[O:23])[CH3:22]>[Fe]>[CH3:15][CH:14]([S:11]([CH2:10][C:6]1[CH:5]=[C:4]([NH:1][C:21](=[O:23])[CH3:22])[CH:9]=[CH:8][CH:7]=1)(=[O:13])=[O:12])[CH3:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A suspension of crude 1-nitro-3-[(propan-2-ylsulfonyl)methyl]benzene (5.0 g) in acetic acid (58 mL) was treated with iron powder (4.7 g), heated for 22 hours at 110° C. bath temperature and cooled to room temperature. Then water (250 mL) and DCM (250 mL) were added, stirred, filtered, dried with sodium sulfate, filtered and concentrated. An analytical sample (200 mg) of the crude title compound (5.6 g) was recrystallized from diethyl ether/ethanol (121 mg). Lit.: [Grohmann and Hathaway, Molbank 2006, M502].
Workup
- temperaturecooled to room temperature
- filtrationfiltered
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customAn analytical sample (200 mg) of the crude title compound (5.6 g) was recrystallized from diethyl ether/ethanol (121 mg)
Sources & evidence
- ORD record
- ord-03d11b2771e24f149965ad6422d46e22
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108926B2
Reaction notes
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