| With many anilines used as precursors in this reaction, the sulfonyl chloride product is a solid and an alternate workup procedure is used. After the
reaction is quenched with ice water, the solid product is filtered with suction and washed copiously with cold water. The crude product tends to
occlude water and copper salts, which may be detrimental in later reactions. A good washing protocol involves rinsing the solid on the filter with
water (200 mL), then suspending the solid in cold water (1000 mL), stirring briskly, and filtering with suction. The latter process should be repeated
three times. The final water wash should be only very slightly yellow. After air drying the product can be recrystallized from an appropriate solvent.
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