m-Chloroperbenzoic acid → HCID 14503119, compound

Participants

Reaction Steps

A solution of m-chloroperoxybenzoic acid (0.10 g, 0.5 mmol) in ethanol (10 mL) was added dropwise to an ice-cooled stirred solution of 41 (0.15 g, 0.5 mmol) in ethanol (25 mL), during 15 min. The reaction mixture was allowed to stand at 0° C. overnight and then evaporated to dryness under reduced pressure. The residue was triturated with a mixture of ethanol (2 mL) and ethyl ether (30 mL). The precipitated crystalline product was collected by filtration and dried at 80° C. for 3 h to yield 70 mg (45%) of the title compound, mp >100° C. (dec.). IR (KBr): 1050 (vs, s, S=O), 3100-3600 (NH2, OH)cm-1 :UV: λmax (pH 1) 330 nm (ε 3,600): λmax (pH 7) 324 nm (4,400): λmax (pH 11) 321 nm 4,300): 1H NMR (DMSO-d6): δ 1.30 (d, 3, CH3), 5.80 (d, 1, J 5.25 Hz, C1'H), 6.51 (s, 2, SONH2, exchanged with D2O), 6.98 (s, 2, NH2, exchanged with D2O), 8.40 (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, 37.98; H, 4.41; N, 26.51; S, 9.91.

Provenance & Evidence