Hydrochloric Acid → n-(3-Bromo-5-phenylsulphanylphenyl)-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 suspension of 0.35 g (0.0025 mol) of thiophenol sodium salt. 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 then heated to 120-130° C. for 20 min., taken up in ethyl acetate and chromatographed on silica gel with ethyl acetate/hexane 1:9 and 1:2. There was obtained 0.085 g (21%) of N-(3-bromo-5-phenylsulphanylphenyl)-N-methylacetamide as a yellow oil. MS (EI): me/e=337, 335 (C15H14BrNOS+).

Provenance & Evidence