Acetic Anhydride → 5-Acetoxy-2-naphthalenesulfonyl chloride

Participants

Reaction Steps

The title compound was prepared using a procedure similar to the procedure used to prepare Example 5. The 5-acetoxy-2-naphthalenesulfonyl chloride was prepared by acylating 0.30 g (1.25 mmol) of 5-hydroxy-2-naphthalenesulfonic acid with acetic anhydride and pyridine. The acetoxysulfonic acid was then treated with POCl3 yielding an orange oil, 0.26 g. The oil was reacted with 0.12 g (0.96 mmol) of the azabicyclononane in CHCl3 solution. The usual work-up gave 270 mg of a green oil. Purification by chromatotron using 8/1/1 hexane/acetone/chloroform gave a yellow oil, 75 mg (22% yield): 1H NMR (CDCl3): 8.34 (d, J=1.5, 1 H, H1), 7.99 (d, J=8.9, 1 H, H3), 7.87 (d, J=8.4, 1 H, H6), 7.78 (d, J=8.9, 1 H, H4), 7.60 (t, J=8.0, 1 H, H7), 7.40 (d, J=7.6, 1 H, H8), 3.29 (d, J=4.2, 4 H, N(CH2R)2), 2.50 (s, 3 H, CH3), 2.08 (s, 2 H, N(CH2CHR)2) 1.74-1.61 (m, 8 H, alkyl H's).

Provenance & Evidence