1-Propanesulfonamide, 3-chloro-N-[(4-nitrophenyl)methyl]- synthesis

Yield:258856-32-5 26%

Reaction Conditions:

with triethylamine in N,N-dimethyl-formamide;

Steps:

R.11 Preparation of 2-(4-Aminobenzyl)-1,1-dioxotetrahydro-2H-1-isothiazole

Reference Example 11 Preparation of 2-(4-Aminobenzyl)-1,1-dioxotetrahydro-2H-1-isothiazole To a solution of 4-nitrobenzylamine hydrochloride (5.00 g) and triethylamine (5.37 g) in DMF (30 ml) was added 3-chloropropylsulfonyl chloride (4.69 g) under ice cooling, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO₄), and the solvent removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give N-(3-chloropropylsulfonyl)-4-nitrobenzylamine (2.00 g, 26%).

References:

US6355672,2002,B1