Pyridine → Acetamide, N-(4-((methylamino)sulfonyl)phenyl)-
Reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N:15]1C=CC=C[CH:16]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][CH3:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a cold (0° C.) suspension of 4-acetamido-benzenesulphonyl chloride (4.0 g, 17 mmol) in CH2Cl2 (40 mL) was added pyridine (1.7 mL, 20 mmol) and DMAP (209 mg, 1.7 mmol). (A clear solution resulted). Anhydrous methylamine was bubbled into the solution for 1 hour at 0° C., and then the solution was allowed to stir at 25° C. for 2 hours. The solution was extracted with 1M NaOH (3×15 mL) and the combined extracts were adjusted to pH 6 at 0° C. with 3M HCl. The product, which precipitated as fluffy white crystals, was filtered and washed with cold water to afford 3.2 g (82%) of 4-acetamido-N-methylbenzenesulphonamide: 1H NMR (300 MHz, MeOH) δ 2.35 (s, 3H), 2.70 (s, 3H), 7.96 (s, 4H).
Workup
- custom(A clear solution resulted)
- customAnhydrous methylamine was bubbled into the solution for 1 hour at 0° C.
- extractionThe solution was extracted with 1M NaOH (3×15 mL)
- customwere adjusted to pH 6 at 0° C. with 3M HCl
- customThe product, which precipitated as fluffy white crystals
- filtrationwas filtered
- washwashed with cold water
Sources & evidence
- ORD record
- ord-644f2c1a14994b6797a43e7f1a204d95
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579890B1
Reaction notes
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