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                 Abstract:
                         New Benzisothiazole Sulfonamide derivatives have been synthesized employing insoluble saccharin (Benzisothiazole) as starting material. Saccharin is first converted into hydroxymethyl  saccharin by reaction with formalin(37%)under reflux. the later was transformed into chloromethyl saccharin by reacting thionyl chloride under anhydrous reaction conditions. sulfonation of this product give an important nucleus Benzisothiazole sulfonic acid.Only specific substituted anilines were selected for sulphonamide formation with this nucleus. reaction of these substituted anilines were performed under reflux for 6-12 hrs to get the desired sulphonamide derivatives. the new Benzisothiazole derivatives and intermediate are characterized by Fourier Transformed Infra Red(FT-IR) and Nuclear MagneticResonance(NMR) Spectroscopy, also by Mass Spectrometry.(this is i have performed)
                 Introduction:
                            Heterocyclic Organo&Biological compounds are most important for drugs synthesis  and industrial state. there are large no of heterocyclic compounds, hetero mean more then one kind of elements included in one ring present in the compound. such type of compound s are usually colourless liquid having character like benzene, resonance stabilized but resonance energy is much lower then that of benzene.

I used Benzisothiazole as starting material in my research project.Saccharin was first produced in 1879 by Constantin Fahlberg, a chemist working on coal tar derivatives in Ira Remsen's laboratory at the Johns Hopkins University, and it was he who, accidentally, discovered its intensely sweet nature..

                            As for as its chemistry is concern.Saccharin has the chemical formula C7H5NO3S and it can be produced in various ways. The original route starts with toluene, but yields from this starting point are low. In 1950, an improved synthesis was developed at the Maumee Chemical Company of Toledo, Ohio. In this synthesis, anthranilic acid successively reacts with nitrous acid, sulfur dioxide, chlorine, and then ammonia to yield  saccharin.
           
                                                      

Strutural formula image

                                                   Molar Mass:183.1845

              Other Parameters. Usually it is marketed as salt of Sodium, Potassium etc                                                                                                                                                                                          

Appearance White crystalline solid

Density

0.828 g/cm3 Melting point 228.8-229.7 °C Solubility in water 1 g per 290 mL

                     Saccharin can be used as sweet,suppressing pain,inhibitors,aqueous drug formulation,slime control,cathodic transformation,paint and dye.  

                 Scientific Approach:
                              In Heterocyclic compound usually the Electrophilic substitution reaction occure,this substitution occur either at Alpha or Beta position but the alpha substitution is preferred because it attributed  to the greater resonance stabilization of the intermediate carbonation formed during alpha substitution compared to the intermediate carbonation formed in the beta substitution.

Because in Benzisothiazole 5-membered hetero ring is very strain and there is inductive effect of C=O and O=S=O groups in this ring, so due to these two reasons amide’s hydrogen is easly replaced by an Electrophile,it mean a large no, of Benzisothiazole derivatives can be formed.Benzisothiazole can be used to prepare exclusively disubstituated amines from alkyl halides via Gabriel synthesis.

                   Experimental work:
                                           In my  research work many organic solvent like benzene, toluene, aniline, ether, acetone etc. were used. As reactants I used analytical reagent grad chemicals like P-Anisidine, P-Chloroaniline, O-Chloroaniline,P-Toluene and O-Amino-benzoic acid. Different synthetic reaction were performed for synthesis of Benzisothiazole derivatives. A brief sketch was out lined in abstract. Here I want to discuss a single reaction out of series of performed reactions, as follow. reaction between sulphonamide derivative of Benzisothiazole and P-Chloroaniline.

                 Procedure:
                             The reaction mixture of Benzisothiazole sulfonic acid (0.5gm, 0.0018moles) and P-Chloroaniline (0.23gm, 0.0018moles) according to ratio 1:1 dissolved in solvent xylene in round bottom flask. the reaction mixture was subjected to reflux for 6 hrs. It was cooled to room temperature, washed the crystals and dried to get the product (0.614gm, 0.00166moles).Confirmed by interpreting Mass spectra, FT-IR spectra and NMR spectra. Calculated yield is 92%.
                          

BENZISOTHIAZOLE SULPHONAMIDE P-CHLOROANILINE DERIVATIVE

REQUIRED DERIVATIVE OF BENZISOTHIAZOLE

As an Organo Chemist and Druggist I can prepare many useful derivatives of my precursor and of resembled structural compounds can be synthesized including drugs and organic heterocyclic compound based on nucleophilic or electrophilic substitution reactions.

                 Importance of saccharin derivatives:
                                               Saccharin derivatives have lot of useful and beneficial  uses especially, as drugs and plasticiser.These have been widely studied for use of phytocide, herbicides and insecticides. imidazolidinetriones are known for their herbicide, plant growth regulator and fungicide properties.