Methanol → Methyl 3-(dimethylsulfamoyl)benzoate

HRID 1777023Notes

Reaction equation

HRID 1777023 reaction equation
[CH3:1][N:2]([CH3:15])[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.[CH3:21]O>>[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:21])=[O:10])(=[O:4])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 49857623-(N,N-dimethylsulfamoyl)benzoic acid

Product 1

HCID 1262217Methyl 3-(dimethylsulfamoyl)benzoate

Procedure

3-(N,N-Dimethylsulfamoyl)benzoic acid (200 mg, 0.872 mmol) was refluxed overnight in the presence of concentrated sulfuric acid (5.64 mg, 0.044 mmol) in methanol (10 mL) at 70° C. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography affording the title compound (125 mg). 1H NMR (400 MHz, CDCl3): δ 8.42 (s, 1H), 8.27 (d, 1H, J=8.0 Hz), 7.97 (d, 1H, J=7.2 Hz), 7.65 (t, 1H, J=8.0 Hz), 3.96 (s, 3H), 2.74 (s, 6H). ESI-MS: 244.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-879914760d094f7bb413181f1cbe02a4
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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