Methyl 4-sulphamoylbenzoate → 4-(Hydroxymethyl)benzenesulfonamide

HRID 2273955Notes

Reaction equation

HRID 2273955 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-6f8748b982314c8b9ac36ce018d0f276
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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