N-Acetylsulfanilyl chloride is used?in the preparation of sulfanilamide and its derivatives which are intermediates to produce sulfa drugs. They are used in the prevention and treatment of bacterial infections, diabetes mellitus, edema, hypertension, and gout. It is also used as a Pharma raw material. N-Acetylsulfanilyl chloride widely used in the fields of dye, medicine, mainly used for preparation of Sulfanilamide, Sulfanilylureal, Sulfatolamide, Sulphathiourea , Sulfaguanidine and Sulfacetamide and etc.
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Acetanilide is introduced into stirred chlorosulfuric acid solution at 20 ℃. The solution is then heated to 55 ℃ and kept at this temperature for 1.5 h. The solution is cooled to 20 ℃ and introduced as a thin jet into water, the temperature of which is kept at 0 – 5 ℃ by external cooling. The precipitated sulfochloride is filtered and washed with cold water until neutral to Congo Red. Yield is 80 – 82%. The crude product contains about 60% water; the dried product melts at 144 – 147 ℃. About 1 – 2% of bis(acetylaminophenyl) sulfone is obtained as a byproduct. If thionyl chloride is added, less chlorosulfuric acid is needed because it can be replaced partly byoleum. The product is stable for several days if kept in a cool place. It is generally used directly in the moist state. 4-(Acetylamino)benzenesulfonyl chloride is an important intermediate in the manufacture of sulfonamides and in the synthesis of parabase ester.
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L-hydroxyproline has been derivatized with N-acetylsulfanilyl chloride and 5-chlorovaleric acid during the synthesis of the haptens HP1 and HP2.
Safety Profile
A poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic vapors of NOx, SOx, and Cl.
Purification Methods
Crystallise the chloride from toluene, CHCl3, or ethylene dichloride. [Beilstein 14 IV 2703.]
