Benzoyl chloride → HCID 135544188, compound

Participants

Reaction Steps

7-Amino-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 6, 200 mg, 0.48 mmol ) was dissolved in dichloromethane (3 mL) and diisopropylethylamine (160 μL, 114 mg, 0.96 mmol) was added. Benzoyl chloride (85 mg, 0.60 mmol ) was then added under nitrogen. The reaction mixture was allowed to stir for 16 h. The suspension was filtered to provide the title compound (120 mg, 0.23 mmol, 48%) as a red solid: NMR (DMSO-d6): δ 16.25 (s, 1H), 10.81 (s, 1H), 8.52 (m, 1H), 8.37 (d, J=9 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 8.02 (d, J=9 Hz, 2H), 7.81 (d, J=9 Hz, 2H), 7.64 (m, 3H), 7.18 (d, J=9 Hz, 2H), 4.82 (m, 1H), 3.83 (s, 3H), 1.25 (d, J=6 Hz, 6H); Analytical HPLC: 95% pure; MS (ES-NEG): [M−H] 518; Anal. Calc. for C27H24N3O6SNa: C, 62.42, H, 4.85, N, 8.09. Found: C, 60.61, H, 4.77, N, 7.70.

Provenance & Evidence