2,6-Dimethoxybenzoyl chloride → HCID 135506372, 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) under nitrogen. 2,6-dimethoxybenzoyl chloride (120 mg, 0.60 mmol) was added and the solution was allowed to stir for 14 h. The resulting suspension was filtered to provide the title -compound (100 mg, 0.17 mmol, 36%) as a red solid: NMR (DMSO-d6): δ 16.30 (s, 1H), 10.81 (s, 1H), 8.35 (s, 1H), 8.21 (d, J=9 Hz, 1H), 7.92 (d, J=9 Hz, 1H), 7.82 (s, 1H), 7.73 (d, J=9 Hz, 2H), 7.21 (t, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 2H), 6.67 (d, J=9 Hz, 2H), 4.72 (m, 1H), 3.87 (s, 3H), 3.82 (s, 6H), 1.32 (d, J=3 Hz, 6H); Analytical HPLC: 88% pure; MS (ES-NEG): [M−H] 578; Anal. Calc. for C29H29N3O8S: C, 60.09, H, 5.04, N, 7.25. Found: C, 57.26, H, 4.82, N, 7.09.

Provenance & Evidence