Methanol → Methyl 3-(methylsulfamoyl)benzoate

HRID 877634Notes

Reaction equation

HRID 877634 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])(=[O:5])=[O:4].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:20])=[O:10])(=[O:4])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2526543-(Methylsulfamoyl)benzoic acid

Product 1

HCID 9320906Methyl 3-(methylsulfamoyl)benzoateYield 53.5%

Procedure

3-(N-methylsulfamoyl)benzoic acid (200 mg, 0.929 mmol) was refluxed in the presence of concentrated sulfuric acid (6.01 mg, 0.046 mmol) in methanol at 70° C. for overnight. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by flash chromatography afforded the methyl 3-(N-methylsulfamoyl)benzoate (120 mg, 0.497 mmol, 53.5% yield). 1H NMR (CDCl3, 400 MHz): δ 8.51 (m, 1H), 8.25 (m, 1H), 8.06 (dt, 1H, J=1.2 & 8.0 Hz), 7.63 (t, 1H, J=7.6 Hz), 3.96 (s, 3H), 2.69 (s, 3H). Mass [M+H]+:230.1

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by flash chromatography

Sources & evidence

ORD record
ord-b9f3dd6557ca451799895352c6cdbf55
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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