Methanol → 4-(Hydroxymethyl)benzenesulfonamide

HRID 1585069Notes

Reaction equation

HRID 1585069 reaction equation
[NH2:1][S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CO.[BH4-].[Li+]>C1COCC1>[OH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 89847Methyl 4-sulphamoylbenzoateHCID 4148881Lithium borohydride

Product 1

HCID 100811624-(Hydroxymethyl)benzenesulfonamideYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [4-(aminosulfonyl)]benzoate (5.8 g, 27 mmol) (Step 2) in THF (400 ml), methanol (1.6 ml, 40 mmol) and lithium borohydride (20 ml, 2M solution in THF, 42 mmol) were added over 10 minutes. After heating at reflux for 3.5 hours, the reaction mixture was cooled and poured over ice containing 1N HCl (80 ml). The reaction mixture was extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated. The crude mixture was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 4-(hydroxymethyl)benzenesulfonamide (3.8 g, 75%) as a white solid.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3.5 hours
  3. temperaturethe reaction mixture was cooled
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-38da7b264fc547689c5dd0464a7fd6fc
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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