Methylamine → 4-Methoxy-N-methylbenzenesulfonamide

HRID 1162448Notes

Reaction equation

HRID 1162448 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][NH2:14]>C(Cl)(Cl)Cl.CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:14][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 74014-Methoxybenzenesulfonyl chloride

Product 1

HCID 24974294-Methoxy-N-methylbenzenesulfonamideYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-methoxybenzene-1-sulfonyl chloride (2.4 g, 12 mmol) in CHCl3 (20 mL) was added methanamine (5 mL, 40 mmol) in EtOH. The mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The resulting solid was washed with H2O (5 mL), ether, and air-dried to give 4-methoxy-N-methylbenzenesulfonamide (1.12 g, 48% yield) as a white solid. MS (ESI positive ion) m/z: 202 (M+1).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washThe resulting solid was washed with H2O (5 mL), ether
  3. customair-dried

Sources & evidence

ORD record
ord-8c91cdf3fb394a8ca5fffbe9726aa7d0
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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