Stannous chloride dihydrate → n-Allyl-3-amino-6-chloro2-hydroxybenzenesulfonamide

HRID 2301521Notes

Reaction equation

HRID 2301521 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-])=O)[C:9]=1[OH:18])(=[O:7])=[O:6])[CH:2]=[CH2:3].O.O.[Sn](Cl)Cl>C(O)C>[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=1[OH:18])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 18373503n-Allyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 18373522n-Allyl-3-amino-6-chloro2-hydroxybenzenesulfonamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-allyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (25 mg, 0.09 mmol) and tin (II) chloride dihydrate (101 mg, 0.44mmol) in 5 mL of ethanol was stirred at room temperature. The mixture was concentrated, the residue was diluted with ethyl acetate and 10% aq. NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give the crude product (20 mg) which was carried on to the next step without purification. EI-MS (m/z) 263.1, 265.2 (M−).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate and 10% aq. NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4940901e9d44b07936605b6c02bba89
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

Loading…