Analogues of Chloramphenicol—Part IV. Synthesis and Biological activity of 2-Dichloroacetamido-1-(4-chloro-3-nitrophenyl) propane- 1,3-diol and Biological activity of 2-Dichloroacetamido-1 -(4-bromo-3-nitrophenyl) propane- 1, 3-diol

Department of Chemistry, Karnatak University, Dharwar-580 003

Manuscript received 9 June 1976, revised 8 November 1976, accepted 10 November 1976

3-Nitro-4-chloro-\(\alpha\)-aminoacetophenone hydrochloride III on treatment with 2,2'-dichloro­acetyl chloride yields the corresponding \(\alpha\)-dichloroacetamido derivative (IV). Hydroxymethyla­tion of IV followed by Meerwein-Poundorf-Verley reduction yields the desired chloramphenicol analogue, dl-threo-2-dichloroacetantido-1-(4-chloro-3-nitropheny-1-)-propane-1,3-diol(VI).