Methanesulfonyl chloride → HCID 10384564, compound

Participants

Reaction Steps

To a solution of 105 mg (0.313 mmol) of 20 in 10 mL of dry dimethyl formamide, were added 66 mg (1.56 mmol) of LiCl and 191 mg (1.56 mmol) of dimethylaminopyrldine. To this mixture was added 120 μL (1.56 mmol ) of methanesulfonyl chloride and the resulting solution gently heated with a heat gun until it became homogenous. After stirring this mixture at room temperature for 6 h, it was combined with 100 mL of water and the resulting mixture allowed to stir for an additional 2 hours. The resulting yellow precipitate was filtered, rinsed with water, and dried: 99 mg (85%) yield; mp >275° C. dec; IR (KBr pellet) 3036, 1645, 1603, 1421, 1372, 1343, 1270, 1240, 1015, 794 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ11.84 (2H, s, 5- and 10-hydroxyl) 4.95 (4H, s, methylenes), 3.65 (6H, s, 3- and 8- methyls); mass spectrum (EI, solids probe), m/z 370 (P+, 35Cl35Cl), 372 (P+, 37Cl35Cl), 374 (P+, 37Cl37Cl). Anal. Calcd for C14H12Cl2N4O4 : C, 45.30, H, 3.26; N, 15.09. Found: C, 45.76; H, 3.47; N, 13.99.

Provenance & Evidence