AFAIK sulfathiazole will not couple with ClCH2CN. Write the structure of your compound.

Can you use iodoacetonitrile instead of chloroacetonitrile?

1-sulfathiazole+HCL and heat untill dissolved.

2-NaNO2+H2O and cooling in ice bath.

3-pyridine+chloroacetonitrile.

then put 2 in 1 and stirring in ice bath.

then put 1 in 3 drop wise.

these are general steps.

-coupling occur on -NH2 to form -N=N-CL then finally form -N=N-CHCL-CN

-I try it for a similar amine (sulfadimidine)and make coupling.

structures attached,

For sulfadimidine

I want to know if there is another method or Is there any precautions?

Hi,

Sulfathiazole + ClCH2CN

The free amino group of sulfathiazole should react very similar to that of para-aminobenzenesulfonamide. Only the free NH2 reacts.

See:

Synthesis, structure analysis and antibacterial activity of new potent sulfonamide derivatives

By Alsughayer, Abdulhakeem; Elassar, Abdel-Zaher A.; Mustafa, Seham; Al Sagheer, Fakhreia

From Journal of Biomaterials and Nanobiotechnology (2011), 2(2), 144-149.

To a solution of 1 (para-aminobenzenesulfonamide) (0.01 mol) in toluene (20 ml) and DMF (10 ml) mixture chloroacetonitrile (0.01 mol) was added. The reaction mixture was heated under reflux for 3 h. The solvent was evaporated under vacuum and the solid product formed after cooling was collected by filtration, washed by ether and crystallized from proper solvent.

PS The sulfadimine should react in the same way.

Bill

thanks william but,

This reaction will produce (-NH-CH-CN) but i want (-N=N-CHCL-CN)

Hi,

OOPS!

Here's a better idea:

get the following paper (interlibrary loan, if you can. What works for the chloroacetate might very well work for the chkoroacetinitrile. There may even be an English translation. The compound I searched was again the sulfonamide of the aniline NH2 (can't attach the structure: ChemDraw name = methyl (E)-2-chloro-2-((4-sulfamoylphenyl)diazenyl)acetate. Note, it's possible that you may get the enantiomer, i.e. ArNHN=C(Cl)COOEt (or CN).

Bill

4. Ethyl arylazochloroacetates and their reactions with morpholine and hydrazine hydrate

By Lozinskii, M. O.; Kukota, S. N.; Pel'kis, P. S.

From Ukrainskii Khimicheskii Zhurnal (Russian Edition) (1967), 33(12), 1295-6

Substituted PhN2Cl reacted with AcCHClCO2Et in MeOH suspension contg. NaOAc at 0-2° to form the following substituted PhN2CHClCO2Et (I) which were recrystd. from MeOH (phenyl substituents and m.p. given): p-MeO, 106-7°; o-EtO, 64-5°; p-EtO, 118-19°; 2,3-Me2, 56-7°; 2,4-Me2, 109-10°; m-Cl, 83-4°; m-I, 126-7°; p-NCS, 160-1°, 2,5-Cl2, 95-6°; o-CO2H, 215-16°; m-CO2H, 184°; p-CO2H, 255-6°; p-MeO2C, 174-5°; p-EtO2C, 150-1°; p-H2NSO2, 186°. I and HN(CH2CH2)2O in refluxing EtOH formed the following substituted PhN2CHQCO2Et (Q = morpholino) (substituents and m.p. given): p-Me, 80-1°; p-Cl, 89-90°; o-O2N, 89-90°. p-O2NC6H4N2CH(NHNH2)CO2Et, m. 168-9°, was similarly prepd. by use of N2H4.H2O.