Sulfuryl chloride → Benzenesulfonyl fluoride, 3-[[[6-chloro-5-hydroxy-8-[[2-(methylsulfonyl)-4-nitrophenyl]azo]-1-naphthalenyl]amino]sulfonyl]-

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Reaction Steps

5-(m-Fluorosulfonylbenzenesulfonamido)-4-(2-methylsulfonyl-4-nitrophenylazo)-1-naphthol (52 g.) (Compound A of Example 13 of U.S. Pat. No. 3,929,760, issued Dec. 30, 1975) is chlorinated by stirring with sulfuryl chloride (200 ml.) for 21 hours at 30°-31° C. The slurry is cooled to 15° and filtered. The resulting solid is then purified by stirring successively with 800 ml. ice water, 100 ml. methanol, 200 ml. acetone (40° C.), and 300 ml. acetone (40°), filtering the resulting slurry each time (acetone precooled to 30°) and washing the solid with the same kind of solvent. The yield is 40.3 g.

Provenance & Evidence