Methylamine → 4-amino-N-methylbenzene-1-sulfonamide

HRID 1064346Notes

Reaction equation

HRID 1064346 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](F)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH2:13]>CCO>[CH3:12][NH:13][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 668234-Aminobenzenesulfonyl fluoride

Product 1

HCID 743684-amino-N-methylbenzene-1-sulfonamideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Aminobenzenesulphonylfluoride (200 mg, 1.14 mmol) was dissolved in a solution of methylamine in EtOH (3 mL, excess) and heated to 80° C. for 45 minutes, then cooled to room temperature and left to stir overnight. The solvent was evaporated in vacuo and azeotroped with ether to yield the title compound as a solid (160 mg, 75%). NMR: 2.12 (s, 3H), 5.85 (s, 2H), 6.59 (d, 2H), 7.37 (d, 2H); m/z 187.

Workup

  1. temperaturecooled to room temperature
  2. waitleft
  3. customThe solvent was evaporated in vacuo
  4. customazeotroped with ether

Sources & evidence

ORD record
ord-d834b28464d74433982306bbd643c04d
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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