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

HRID 2240774Notes

Reaction equation

HRID 2240774 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 rt 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. extractionThe mixture is extracted with EA
  3. extractionthe organic extract
  4. washis washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customthe crude product is purified by CC on silica gel eluting with DCM containing 5% of methanol

Sources & evidence

ORD record
ord-2f5f473d283a47818c36666c06a8fca0
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

Loading…