Hydrochloric Acid → 3-(Hydroxymethyl)benzene-1-sulfonamide

HRID 916813Notes

Reaction equation

HRID 916813 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:4])=[O:3].Cl>CO>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2293523-Sulfamoylbenzoic acid

Product 1

HCID 231337993-(Hydroxymethyl)benzene-1-sulfonamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Aminosulfonyl)benzoic acid (2.18 g) was stirred with ice-water cooling and under nitrogen while borane-THF complex (32.5 ml) was added dropwise over 15 min. After 2 h at 22° further borane-THF complex (16 ml) was added. After a further 2 h the mixture was cooled with ice-water and methanol (40 ml) was added dropwise. After 15 min 2M hydrochloric acid (90 ml) was added and the mixture was left to stand at 21° overnight. The solution was extracted 3 times with ethyl acetate and the organic layers were combined and washed twice with brine, dried (MgSO4) and concentrated. This solution was loaded onto a column of silica gel (200 g) and the column was run with ethyl acetate and then 10% methanol in ethyl acetate to give the title compound (1.595 g), LCMS RT=0.83 min.

Workup

  1. additionwas added dropwise over 15 min
  2. additionAfter 2 h at 22° further borane-THF complex (16 ml) was added
  3. additionwas added dropwise
  4. waitthe mixture was left
  5. extractionThe solution was extracted 3 times with ethyl acetate
  6. washwashed twice with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-66989107d4a74cbaa990d9eff9574ede
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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