HCID 10198942, compound → HCID 15888357, compound

Participants

Reaction Steps

To a cooled mixture of 3-bromo-1,2,4-thiadiazolo[4,5-a]benzimidazole (4.55 g, 17.9 mmole) in 50 mL of methanol, sodium methoxide (0.967 g, 17.9 mmole) was added in one portion and stirred for 4 h at room temperature. The reaction mixture was evaporated to dryness under vacuum and the residue was taken-up in ethyl acetate and washed with water. The organic layer was dried with sodium sulfate, filtered and evaporated to yield 3.64 g (94%) of 3-methoxy-1,2,4-thiadiazolo[4,5-a]benzimidazole as colourless crystals: mp 172-175° C.; 1H NMR (CDCl3) δ 7.83 (d, 1H), 7.75 (d, 1H), 7.42 (t, 1H), 7.27 (t, 1H), 4.32 (s, 3H) ppm; 13C NMR (CDCl3) δ 163.2, 150.3, 148.1, 128.119.2, 111.7, 57.5119.2, 111.7, 57.5 ppm; IR (KBr) ν 3418, 2942, 1595, 1492, 1404, 1275, 1255, 1206, 1083, 755 cm-1. Anal. Calcd for C9H7N3OS: C, 52.67; H, 3.44; N, 20.49. Found: C, 52.28; H, 3.36; N, 20.45.

Provenance & Evidence