Methanol → Benzoic acid, 3-(aminosulfonyl)-, methyl ester

HRID 734736Notes

Reaction equation

HRID 734736 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH3:14]O>S(=O)(=O)(O)O.CCOC(C)=O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:14])=[O:9])(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 2293523-Sulfamoylbenzoic acid

Product 1

HCID 108836Benzoic acid, 3-(aminosulfonyl)-, methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(Aminosulfonyl)benzoic acid (603 mg, 3.0 mmol) was heated at 80° C. in CH3OH (3 mL) with 3 drops of concentrated sulfuric acid for 60 hours. The reaction mixture was diluted with EtOAc (20 mL), washed with water, brine, and dried (Na2SO4). The solvent was evaporated to afford the product (630 mg, 98%) as a white solid. MS (ES+) m/z 216 [M+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a4b72a81d93e43e8aa724688c2f86acf
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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