4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenoxysulfonyl}-2-hydroxy-benzoic Acid

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Reaction Steps

The title compound was prepared according to the procedure in Example 4 using 4-[(2-butyl-benzofuran-3-ylmethyl)-amino]-phenol (0.500 g, 1.69 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.401 g, 1.69 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 25% EtOAc/hexane gave 0.571 g (85%) of the title compound as a dark yellow solid, mp 75-77° C. 1H NMR (DMSO-d6) δ0.86 (t, 3H), 1.31 (sextet, 2H), 1.60 (quintet, 2H), 2.80 (t, 2H), 4.23 (s, 2H), 6.54 (d, 2H), 6.72 (d, 2H), 7.14-7.22 (m, 2H), 7.26-7.30 (m, 2H), 7.45 (dd, 1H), 7.58 (dd, 1H), 7.95 (d, 1H). IR (KBr) 3400, 2950, 1600, 1510 and 1380 cm−1. mass spectrum (−ESI) m/z 494 (M−H).

Provenance & Evidence