Sodium borohydride → 2-Amino-5-(1-hydroxyethyl)benzenesulfonamide

HRID 496101Notes

Reaction equation

HRID 496101 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:14])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CCO>[NH2:14][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][C:8]=1[S:10]([NH2:13])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 129523995-Acetyl-2-aminobenzenesulfonamide2×

Product 1

HCID 223240092-Amino-5-(1-hydroxyethyl)benzenesulfonamideYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-Acetyl-2-aminobenzenesulfonamide (see compound 13) (0.95 g, 4.4 mmol) was suspended in 96% o EtOH (50 ml) and NaBH4 (0.46 g, 12 mmol) was added in one portion. The mixture was stirred at 25° C. for 4 h and filtered through Celite and the solvent was removed under reduced pressure. The residue was treated with sat. NaHCO3 (50 ml) and extracted with EtOAc (2×50 ml), dried (Na2SO4) and evaporated to dryness. Flash-chromatography with EtOAc:n-hexane:Et3N (200:100:4, v/v/v) as eluent gave 0.35 g (37%) of 2-amino-5-(1-hydroxyethyl)benzenesulfonamide as light-brown powder. M.p. 160-162° C.

Workup

  1. additionwas added in one portion
  2. filtrationfiltered through Celite
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was treated with sat. NaHCO3 (50 ml)
  5. extractionextracted with EtOAc (2×50 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c47a93b3a62f4ca0b6bcb01c860988f8
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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