Methylamine → 4-(Methylsulfamoyl)benzoic acid

HRID 2240773Notes

Reaction equation

HRID 2240773 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][NH2:15]>C(Cl)Cl>[CH3:14][NH:15][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 5060564-(Methylsulfamoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chlorosulfonylbenzoic acid (5.8 g, 25.2 mmol) in DCM (200 mL), a solution of methylamine (52.15 mL, 2 M in THF) is added. The mixture is stirred overnight at rt before the solvent is evaporated. The residue is dissolved in sat. aq. NH4Cl solution and extracted with EA. The organic extract is washed with water, dried over MgSO4, filtered and the solvent of the filtrate is evaporated to give 4-methylsulfamoyl-benzoic acid (3.77 g) as a white solid; LC-MS: tR=0.64 min.

Workup

  1. customis evaporated
  2. dissolutionThe residue is dissolved in sat. aq. NH4Cl solution
  3. extractionextracted with EA
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-c9f763799bb445d0816a4359cfc59e14
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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