Methylamine → 2-Hydroxy-5-methylsulfamoyl-benzoic acid

HRID 1352271Notes

Reaction equation

HRID 1352271 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([OH:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[CH3:15][NH2:16]>ClCCl>[OH:14][C:8]1[CH:7]=[CH:6][C:5]([S:2](=[O:4])(=[O:3])[NH:16][CH3:15])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27772405-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 144900612-Hydroxy-5-methylsulfamoyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 63 mmol 5-chlorosulfonyl-2-hydroxy-benzoic acid in 120 ml dichloromethane at RT was added dropwise 317 mmol methylamine (8 M solution in ethanol) and the mixture was allowed to stir at RT for 1 h. The mixture was then concentrated in vacuo. The residue was suspended in 1 M aq NaOH solution and extracted twice with ether. The aqueous phase was acidified with 5 M aq HCl, saturated with NaCl, and extracted 3 times with THF. The combined THF extracts were washed twice with saturated aqueous NaCl solution and dried with Na2SO4. Evaporation in vacuo yielded the title compound. MS (m/e): 249.0 (M+NH4+, 100%), 231.9 (M+H+, 63%)

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionextracted twice with ether
  3. extractionextracted 3 times with THF
  4. washThe combined THF extracts were washed twice with saturated aqueous NaCl solution
  5. dry with materialdried with Na2SO4
  6. customEvaporation in vacuo

Sources & evidence

ORD record
ord-e24bcf21ece54761ab4d09af8cd8c6c9
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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