Methylamine → 4-Methoxy-N-methylbenzenesulfonamide

HRID 2077508Notes

Reaction equation

HRID 2077508 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>[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

4

Reactant 2

HCID 6329MethylamineHCID 74014-Methoxybenzenesulfonyl chloride

Product 1

HCID 24974294-Methoxy-N-methylbenzenesulfonamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzene-1-sulfonyl chloride (688.1 mg, 3.331 mmol) was suspended in DCM (10 mL) and methylamine (6.5 mL, 2.0 M in THF, 13 mmol) was added. The reaction was stirred under nitrogen for about 80 minutes. The mixture was filtered, and the solid was washed with DCM. The filtrate was concentrated and dried under high vacuum to provide 4-methoxy-N-methylbenzenesulfonamide (497 mg, 74% yield). MS (ESI pos. ion) m/z: 202 (MH+). Calculated exact mass for C8H, NO3S: 201.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with DCM
  3. concentrationThe filtrate was concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-03c4bcb6bf614512a1b497a1b4ad345e
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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