4-(Methylsulfamoyl)benzoic acid → Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl-

HRID 1665912Notes

Reaction equation

HRID 1665912 reaction equation
B.C1COCC1.[CH3:7][NH:8][S:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C1COCC1.Cl>[OH:17][CH2:16][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH3:7])(=[O:11])=[O:10])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 5060564-(Methylsulfamoyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 17981768Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl-Yield 48.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., borane-THF complex (66.8 mL, 1 M in THF) is carefully added to a solution of 4-methylsulfamoyl-benzoic acid (3.56 g, 16.5 mmol) in THF (90 mL). The mixture is refluxed for 1.5 h, cooled to it and diluted with 1 N aq. HCl (175 mL). The mixture is extracted with EA and the organic extract is washed with sat. aq. NaHCO3, dried over MgSO4 and filtered. The filtrate is concentrated and the crude product is purified by CC on silica gel eluting with DCM containing 5% of methanol to give 4-hydroxymethyl-N-methyl-benzenesulfonamide (1.61 g) as a colourless oil; LC-MS: tR=0.56 min, [M+1+CH3CN]+=243.14.

Workup

  1. temperatureThe mixture is refluxed for 1.5 h
  2. temperaturecooled to it
  3. extractionThe mixture is extracted with EA
  4. extractionthe organic extract
  5. washis washed with sat. aq. NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated
  9. customthe crude product is purified by CC on silica gel eluting with DCM containing 5% of methanol

Sources & evidence

ORD record
ord-30e2a43dbe1a4d67b160e3d7984dd478
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

Loading…