Pyridine → 4-bromo-N-methylbenzene-1-sulfonamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:12]1C=CC=C[CH:13]=1.CN>C(Cl)Cl>[CH3:13][NH:12][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-bromophenylsulfonyl chloride (25.5 g, 100 mmol), CH2Cl2 (400 mL) and pyridine (1.6 g, 110 mol) was cooled to 0° C. and methylamine gas was added over 45 minutes. The mixture was warmed to room temperature, the solvent was removed in vacuo and the residue was dissolved in CH2Cl2 and washed with 2N HCl (2×100 mL), water (1×200 mL), saturated NaHCO3 (1×200 mL) and then brine (1×200 mL). The solvent was dried over MgSO4 and the solvent was removed in vacuo to afford 23 g of N-methyl-4-bromophenylsulfonamide.
Workup
- temperatureThe mixture was warmed to room temperature
- customthe solvent was removed in vacuo
- dissolutionthe residue was dissolved in CH2Cl2
- washwashed with 2N HCl (2×100 mL), water (1×200 mL), saturated NaHCO3 (1×200 mL)
- dry with materialThe solvent was dried over MgSO4
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-192ca6e62625452e852b21588572cde7
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380721
Reaction notes
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