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Chlorosulfonyl-containing naphthol azo com-pounds were prepared by reaction of the corresponding sulfonate-containing naphthol azo dyes with thionyl chloride in the presence of a catalytic quantity of N,N-dimethylformamide and various solvents. The yields and reaction selectivity of chlorosulfonyl-containing naphthol azo compounds were discussed according to the prop-erties of solvents. It was demonstrated that high chemical selectivity and high yield were achieved by using benzene, toluene or thionyl chloride as solvent. Additionally, on account of unstable properties of sulfonyl chloride com-pounds in MS and 1H-NMR analyses, a new analytical method using stable sulfonamide is put forward to verify the chemical structures of the corresponding sulfonyl chloride compounds indirectly.