Methanol → Methyl 3-(dimethylsulfamoyl)benzoate

HRID 877608Notes

Reaction equation

HRID 877608 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-df478f5fe3d74dc29b77ac33dd68c4c2
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

Loading…