Ethanolamine → 3-amino-N-(2-hydroxyethyl)benzenesulfonamide

3-Nitrobenzenesulfonyl chloride (2.22 g) dissolved in 20 mL of THF was added to a solution of 2-aminoethanol (2.0 g) and tryethylamine (2.0 g) in 20 mL of THF. The reaction mixture was kept at ambient temperature overnight. The solvent was removed and the residue was dissolved in water (20 mL) and then extracted with EtOAc (2×50 mL). The solvent of the organic layer was removed and the residue was dissolved in 50 mL of EtOH and a catalytic amount of Raney-Nickel was added, followed by the addition of hydrazine hydrate (2 mL). The reaction mixture was kept at ambient temperature under argon overnight, filtered through a celite cake. The solvent of the filtrate was removed yielding 1.1 g of 3-amino-N-(2-hydroxyethyl)benzenesulfonamide which was used in the next step without further purification.

1. customThe solvent was removed
2. dissolutionthe residue was dissolved in water (20 mL)
3. extractionextracted with EtOAc (2×50 mL)
4. customThe solvent of the organic layer was removed
5. dissolutionthe residue was dissolved in 50 mL of EtOH
6. additiona catalytic amount of Raney-Nickel was added
7. additionfollowed by the addition of hydrazine hydrate (2 mL)
8. waitThe reaction mixture was kept at ambient temperature under argon overnight
9. filtrationfiltered through a celite cake
10. customThe solvent of the filtrate was removed

ORD record

ord-585f52aa25624613a6639c4435d5a62e

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105503B2