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

HRID 1767611Notes

Reaction equation

HRID 1767611 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% 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. filtrationfiltered through Celite
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was treated with sat. NaHCO3 (50 ml)
  4. extractionextracted with EtOAc (2×50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-016282ee02e6456dabde5507e856f167
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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