Hydrochloric Acid → N-[3-[2-(phenylsulphonyl)-diazenyl]-5-bromophenyl]-N-methylacetamide

Participants

Reaction Conditions

Reaction Steps

0.243 g (0.001 mol) of N-(3-amino-5-bromophenyl)-N-methylacetamide was suspended in 5 ml of water, treated with 0.2 ml (0.002 mol) of HCl (37%) and cooled to 0° C. A solution of 0.069 g (0.001 mol) of NaNO2 in 1 ml of water was added thereto, the mixture was stirred at 0° C. for 5 min. and subsequently at room temperature for 10 min. and finally treated with a solution of 0.25 g (0.0015 mol) of benzenesulphinic acid sodium salt in 5 ml of water. The reaction mixture was treated in an ultrasound bath for 10 min. and subsequently partitioned in water/ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and freed from solvent. The residue was chromatographed on silica gel with 1% MeOH in dichloromethane. There was obtained 0.23 g (58%) of N-[3-[2-(phenylsulphonyl)-diazenyl]-5-bromophenyl]-N-methylacetamide as a brown oil. MS (ISN): me/e=456, 454 (C15H14BrN3O3S- +NaOAc).

Provenance & Evidence