3-Chloro-4-morpholino-1,2,5-thiadiazole

Brown Solid

Add morpholine(6.75g, 77.4 mmol) to a 100-mL 3-neck flask equipped with a reflux condenservia syringe. The flask was heated to 110 °C, and 3, 4-dichloro-1, 2, 5-thiadiazole(3.0 g, 19.3 mmol) was added dropwise over the course of 20 min . Once additionwas complete, the reaction was stirred at 110 °C for 2 hours. The reactionmixture was cooled to 0 °C in an ice bath. Water (30 mL) was added and themixture was made acidified with concentrated hydrochloric acid. The mixture wasstirred at 0 °C and a precipitatecrashed out of solution. The solids werefiltered, washed with water, and dried.The orange solid was recrystallized from methanol and dried under highvacuum to yield 3.5 g (87.9percent) of 4-(4-chloro-1, 2, 5-thiadiazol-3-yl)morpholine. General procedure: Sulfur monochloride (0.32 mL, 4 mmol) was added dropwise to a solution of phenylglyoxime 1a (164 mg, 1 mmol) andpyridine (0.48 mL, 6 mmol) in dry acetonitrile (10 mL) at –30 °C.The reaction mixture was warmed up to room temperature, keptfor 20 h, heated at 82 °C for 4 h, cooled down, and filtered. Thefiltrate was diluted by dichloromethane (20 mL), washed withwater (3×20 mL), and dried over anhydrous magnesium sulfate.The solvent was evaporated, the residue was purified by columnchromatography over silica (eluent petroleum ether—dichloromethane, initially 5 : 1, then 1 : 1).

An intermediate for the synthesis of Timolol

Molecular Weight:205.67
XLogP3:1.4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:205.0076608
Monoisotopic Mass:205.0076608
Topological Polar Surface Area:66.5
Heavy Atom Count:12
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes