3-((3-(Trifluoromethyl)phenyl)sulfonyl)-2-propenenitrile. The compound has antimicrobial utility.

DESCRIPTION OF KNOWN PRIOR ART 
S. A. Heininger et al., in U.S. Pat. No. 3,159,532, patented Dec. 1, 1964, 
discloses phenylsulfonyl alkenenitriles which are said to inhibit the 
growth of microorganisms such as bacteria and fungi. Compounds such as 
3-(4-chlorophenylsulfonyl)acrylonitrile and analogs thereof having on the 
phenyl nucleus other halo or lower alkyl substitution are disclosed. S. U. 
K. A. Richter, in U.S. Pat. No. 3,541,119, patented Nov. 17, 1970, 
discloses benzenesulfonylacrylonitrile and homologs and analogs thereof 
having halo or lower alkyl or p-acetamido substitution on the benzene 
nucleus. The compounds are said to have bioactive properties. S. U. K. A. 
Richter, in U.S. Pat. No. 3,821,399, discloses that certain 
phenylsulfonylacrylonitriles wherein the phenyl moiety has at least one 
substituent selected from amino, acylamido or nitro and, optionally, a 
second lower alkyl substituent on the phenyl moiety, prevent the growth of 
microorganisms. 
SUMMARY OF THE INVENTION 
The new compound 3-((3-(trifluoromethyl)-phenyl)sulfonyl)- 2-propenenitrile 
having the formula 
##STR1## 
is prepared by mixing together m-trifluoromethylbenzenesulfonyl chloride 
with excess acrylonitrile, a small proportion of acetonitrile and a 
catalytic amount of cupric chloride together with triethylamine 
hydrochloride as catalyst in a cooled, evacuated vessel, submersing the 
latter in an oil bath at about 110.degree. C. to substantial completion of 
reaction (ca. 3 days), stripping the solvents, and then treating the 
resulting amber oil with methanol and extracting with methylene chloride. 
The extract, a mixture of 3-((3-(trifluoromethyl)phenyl)-sulfonyl)- 
2-propenenitrile and 
3-((3-(trifluoromethyl)-phenyl)sulfonyl)-2-chloropropanenitrile was 
treated with excess triethylamine in benzene at a low temperature, 
by-product triethylamine hydrochloride was filtered off and the solvent 
was removed to give a white crystalline product, which upon 
recrystallization from methanol, gave the title product, melting at 
79.degree.-80.degree. C.

DESCRIPTION OF SOME PREFERRED EMBODIMENTS 
The inventive product has antimicrobial activity. In the conventional in 
vitro agar Petri dish dilution test for determining bactericidal and 
fungicidal activity, the compound gave 100% inhibition against the 
indicated organisms at the following concentrations in parts per million, 
the tabulated values being indicated as minimum inhibitory concentrations 
(MIC). 
TABLE 
______________________________________ 
3-((3-(Trifluoromethyl)phenyl)sulfonyl)-2-propenenitrile 
Minimum Inhibitory Concentration, ppm 
S. aureus 5 
C. albicans 50 
T. mentagrophytes 10 
K. pneumoniae M-1 Midland Hospital 
50 
P. chrysogenum 50 
A. niger 50 
B. subtilis 5 
C. pelliculosa 10 
P. pullulans 50 
S. typhosa 5 
Pseudomonas Sp. Strain 10 100 
C. ips 10 
Trichoderm Sp. Madison P-42 
50 
S. marcescens NIH 50 
Torulopsis Species 50 
A. fumigatus 50 
C. albicansNIH 50 
E. coli ATCC 11229 50 
______________________________________ 
the following additional descriptive example further describes the 
invention and the manner and process of making and using it to enable the 
art skilled to make and use the same and sets forth the best mode 
contemplated by the inventors of carrying out the invention. 
EXAMPLE 
3-((3-(Trifluoromethyl)phenyl)sulfonyl)-2-propenenitrile 
##STR2## 
A 12.4 g (0.05 mol) portion of m-trifluoromethylbenzenesulfonyl chloride 
was introduced into a 100 ml Fisher-Porter reaction vessel along with 5.3 
g (0.1 mol) of acrylonitrile, 2 ml of acetonitrile, 0.07 g of cupric 
chloride and 0.11 g of triethylamine hydrochloride as catalyst. After 
cooling and evacuation at 2 mm Hg, the vessel was submersed in an oil bath 
at 110.degree. C. for three days. After stripping the solvents, an amber 
oil was recovered which on treatment with aqueous methanol and extraction 
with methylene chloride gave 10.0 g of a light amber oil. The extracted 
oil proved to be a mixture of the 3-arylsulfonyl-2-propenenitrile product 
and 3-arylsulfonyl-2-chloropropanenitrile. Treatment of this mixture with 
excess triethylamine in benzene at 10.degree. C, followed by filtration of 
the amine hydrochloride and removal of solvent, afforded 3.7 g of white 
crystals upon recrystallization from methanol, m.p. 79.degree.-80.degree. 
C. 
Anal. Calcd. for C.sub.10 H.sub.6 F.sub.3 NO.sub.2 S: C, 46.4; H, 2.3; N, 
5.3. Found: C. 46.04; H, 2.3; N, 5.5. 
The m-trifluoromethylbenzenesulfonyl chloride starting material was 
prepared by reacting benzotrifluoride with chlorosulfonic acid in the 
presence of oleum (65% SO.sub.3), according to the method described in 
Chemical Abstracts 75, 19942d, (1971); German Offen. No. 1,954,448.