m-Chloroperbenzoic acid → HCID 14657015, compound

Participants

Reaction Steps

A solution of m-chloroperoxybenzoic acid (0.50 g, 2.5 mmol) in ethanol (50 mL) was added dropwise to an ice-cooled (0°-5° C.), stirred solution of 45 (0.75 g, 2.5 mmol) in ethanol (150 mL), during 15 min. The reaction mixture was allowed to stand at room temperature overnight and the crystalline product that deposited was collected by filtration. The product was washed with ethanol (2×15 mL) and air-dried to yield 0.24 g (31%) of 46. mp 178° C. (dec.). IR (KBr): 1040, 1300 (s, S=O), 3100-3600 (NH2, OH)cm-1 ; UV: λmax (pH 1) 329 nm (ε 3,800): λmax (pH 7) 323 nm (ε 5,800): λmax (pH 11) 323 nm (ε 3,700): 1H NMR (DMSO-d6): δ 6.27 (dd, 1, J=5.5 Hz, C1'H), 6.50 (s, 2, SONH2, exchanged with D2O), 6.94 (s, 2, NH2, exchanged with D2O), 8.43 (s, 1, C8H), and other sugar protons. Anal. Calcd. for C10H14N6O4S (314.32): C, 38.21; H, 4.49; N, 26.74; S, 10.20. Found: C, 38.34; H, 4.59; N, 26.47; S, 10.17.

Provenance & Evidence