Pyridine → 4-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

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Reaction Steps

Chloro-acetyl chloride (3.3 mL, 40.8 mmol) was added with stirring to a solution of the ester of Example 35j (5 g, 13.6 mmol) in CH2Cl2 (100 mL) at 15° C., followed by addition of pyridine (6.6 mL, 81.6 mmol). The reaction mixture was stirred for 2 h, concentrated, treated with water and the solid that precipitated was filtered and purified by refluxing it with stirring in ethyl acetate for 0.5 h. The solid was filtered and dried to obtain the title compound. Yield: 5.5 g, (90.9%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 4.31 (s, 2H, CH2), 5.4 (s, 2H, CH2), 7.71 (s, 1H, Ar), 7.98 (s, 1H, Ar), 8.12 (s, 1H, Ar), 8.2 (s, 1H, Ar), 10.77 (s, 1H, Ar); MS: m/e (ES−) 442(M−1).

Provenance & Evidence