Sulfuric Acid → HCID 9843842, compound

Participants

Reaction Conditions

Reaction Steps

To a solution consisting of 15 mL of acetic acid and 0.5 mL of sulfuric acid, was added 333 mg (0.766 mmol) of 12. The resulting mixture was heated at 110° C. for 5.5 hours. After cooling the reaction mixture to room temperature, the solution was poured over ca 50 mL of water and then buffered to pH 6 with sodium acetate. The resulting yellow precipitate was filtered, washed with water, and then dried. The dried solid was recrystallized from ethanol: 219 mg (72%) yield; mp 273°-274° C.; TLC (ethyl acetate/methanol [9:1]), Rf =0.34; IR (KBr) 1677, 1607, 1434, 1347, 1324, 1269, 1071, 1032, 795, 690 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ4.92 (4H, s, methylenes), 3.95 (6H, s, methoxys), 3.59 (6H, s, 3- and 8- methyls); mass spectrum (EI), m/z 398 (P+, 35Cl35Cl), 400 (P+, 37Cl35Cl), 402 (P30, 37Cl37Cl37). Anal. Calcd for C16H16Cl2N4O4 : C, 48.14; H, 4.04; N, 14.03. Found: C, 48.40; H, 4.03; N, 14.14.

Provenance & Evidence