Methyl 4-sulphamoylbenzoate → 4-(Hydroxymethyl)benzenesulfonamide

HRID 1396042Notes

Reaction equation

HRID 1396042 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:6][CH:5]=1.[BH4-].[Li+]>C1COCC1.CO>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:11])(=[O:12])=[O:13])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 89847Methyl 4-sulphamoylbenzoateHCID 4148881Lithium borohydride

Product 1

HCID 100811624-(Hydroxymethyl)benzenesulfonamideYield 17%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.2 g 4-sulfamoyl-benzoic acid methyl ester in 100 mL THF and 1.44 mL MeOH, 0.77 g lithium borohydride was added portion-wise over a period of 10 minutes. The mixture was heated at reflux overnight, cooled to room temperature, and poured onto ice containing 100 mL 1N HCl. The mixture was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by automated flash chromatography (EtOAc/Hexane 1:1) to give 0.75 gram (17%) of product. 1H NMR (400 MHz, DMSO-d6) δ 4.57 (d, J=5.81 Hz, 1H), 5.38 (t, J=5.81 Hz, 1H), 7.48 (d, J=8.34 Hz, 2H), 7.78 (d, J=8.34 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. additionpoured onto ice containing 100 mL 1N HCl
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by automated flash chromatography (EtOAc/Hexane 1:1)

Sources & evidence

ORD record
ord-14d4b6c8071e412daae7ce5b7cf8cbbe
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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