103. N-Acetylsulfanilyl Chloride

Nomenclature

CAS number: 121-60-8
4-(Acetylamino)benzenesulfonyl chloride; p-acetamidobenzenesulfonyl chloride; p-acetaminobenzenesulfonyl chloride; acetanilide-p-sulfonyl chloride; ASC.
C8H8ClNO3S; mol wt 233.67.
C 41.12%, H 3.45%, Cl 15.17%, N 5.99%, O 20.54%, S 13.72%.

Description and references

Prepd by sulfonation of acetanilide: Stewart, J. Chem. Soc. 121, 2558 (1922); Smiles, Stewart, Org. Synth. coll. vol. I, 8 (2nd ed., 1941).

Chemical structure

Properties

Thick, light tan prisms from benzene, mp 149°. Has slight odor of acetic acid. Benzene and ether are poor solvents for purification by recrystn. Much better results are obtained using chloroform or ethylene dichloride. Cf. Northey, Sulfonamides (New York, 1948) p 12.

Caution

Irritant to skin, eyes, and mucous membranes of nose and throat.

Use

Intermediate in the prepn of sulfanilamide and its derivs.