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Systematic (IUPAC) name
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
CAS number 5560-78-1
ATC code P01AC04
PubChem CID 21723
ChemSpider 20418
KEGG D06051 YesY
Chemical data
Formula C20H28Cl4N2O4 
Mol. mass 502.26 g/mol
 YesY (what is this?)  (verify)

Teclozan is an antiprotozoal agent.

It is a dichloroacetamide,[1] (c.f. chloramphenicol and Cetophenicol).


The synthesis begins with alkylation of the alkoxide derived from ethanolamine with ethyl iodide to give the aminoether.

Reaction of 1,4-bis(bromomethyl)benzene with 2-nitropropane in the presence of base leads to dialdehyde.

The reaction probably proceeds by O-alkylation on the nitropropyl anion followed by bond reorganization and subsequent hydrolysis of the resulting enol ether.

Teclozan synthesis:[2]

Reductive alkylation of the dialdehyde with aminoether gives diamine. Acylation by means of dichloroacetyl chloride affords teclozan.


The presence of the dichloroacetamide grouping is apparently not an absolute requirement for antiamoebic activity.

Symetine synthesis: K. Gerzon and E. R. Shepard, U.S. Patent 2,759,977 (1956); Chem. Abstr., 51: 3664a (1956).

Reductive amination of dialdehyde with n-hexylamine followed by Eschweiler–Clarke methylation by heating with formaldehyde in formic acid then leads to the antiamoebic drug symetine.


  1. ^ Slighter RG, Yarinsky A, Drobeck HP, Bailey DM (August 1980). "Activity of quinfamide against natural infections of Entamoeba criceti in hamsters: a new potent agent for intestinal amoebiasis". Parasitology 81 (1): 157–68. doi:10.1017/S0031182000055128. PMID 6252530. 
  2. ^ Surrey, Alexander R. (1961). "New Amorbacides--VI. The Preparation of some N,N'-Disubstituted-N,N'-bis(haloacyl)-1,4-xylylenediamines". Journal of Medicinal and Pharmaceutical Chemistry 3 (3): 409–417. doi:10.1021/jm50016a001.  edit