3,5-Dibromo-1H-1,2,4-triazole

Pale yellow or white powder

To a solution of 1, 2, 4-triazole, 1 (27.6 g, 399.6 mmol) in dichloromethane (80 mL) was simultaneously added bromine in dichloromethane (50percentv/v, 80 mL) and an aqueous solution of sodium hydroxide (50percent w/v, 96 mL). The rate of addition was such that the temperature of the reaction mass was maintained between 10-15°C. After the complete addition, the temperature was raised to 25°C and the stirring was continued for an additional 12 h. Into this was then added 6 N aq.HCl and stirring continued for 1 h.The solid thus precipitated was filtered, and dried under vacuum at 50°C to afford 2 as an off-white solid(80 g, 90percent). The product was used without further purification.Intermediate 1 3, 5-Dibromo-lH-l, 2, 4-triazole Solutions of bromine (6.1 mL, 119 mmol) in DCM (15 mL) and sodium hydroxide (6.78 g, 169 mmol) in water (20 mL) were simultaneously added dropwise to a stirred mixture of 1H-1, 2, 4- triazole (3.9 g, 56 mmol), water (50 mL) and DCM (15 mL) at 0°C while keeping the reaction temperature below 20°C. The mixture was stirred at ambient temperature over night. Hydrochloric acid (cone, 2.0 mL, 66 mmol) was added. The solid was isolated by filtration, washed with water and dried in vacuum to yield the title compound as a solid (8.3 g, 65percent). MS (ESI ) m/z 224 [M-H]Intermediate 1 3, 5-Dibromo-lH-l, 2, 4-triazole lH-l, 2, 4-Triazole (3.9 g, 56 mmol) was mixed in water (50 mL) and DCM (15 mL) at 0°C. A solution of dibromine (6.1 mL, 119 mmol) in DCM (15 mL) and a solution of sodium hydroxide (6.78 g, 169 mmol) in water (20 mL) were added dropwise simultaneously while keeping the reaction temperature below 20°C. The mixture was stirred at ambient temperature over night. Hydrochloric acid (cone, 2.0 mL, 66 mmol) was added. The solid was isolated by filtration, washed with water and dried under vacuum to yield the title compound as a solid (8.3 g, 65percent). MS (ESI ) m/z 224 [M-H]Weigh the raw material A mixture of compound j (5.00 g, 22.0 mmol, 1.00 eq), compound i (5.45 g, 26.5 mmol, 1.20 eq), Cu(OAc)2 (6.00 g, 33.1 mmol, 1.50 eq), Py (5.23 g, 66.1 mmol, 5.34 mL, 3.00 eq) and 4A MS (3.00 g, 22.0 mmol, 1.00 eq) in toluene (75 mL) was degassed and purged with O2 for 3 times, and then the mixture was stirred at 90C for 6 hr under O2 atmosphere. The resulting mixture was cooled, then filtered with celite, washed with ethyl acetate (50 mL), then the solution was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2, Petroleum ether/Ethyl acetate = 100/1 to 5: 1). Compound k (4.97g, 97.15% purity) was obtained as a yellow oil and confirmed by LCMS (EW12195-115-P1C), HNMR. LC-MS (ESI): m/z (M+H) 387.7; NMR (400MHz, CDCb) d = 7.65 - 7.60 (m, 2H), 7.41-7.37 (m, 2H).15.38 g (67.79 mmol) of chloroacetone (0.7 mL, 8.8 mmol) was slowly added to a solution of Sodium tert-butoxide (372 mg, 3.9mmol) was added to a solution of A solution of N-chloroethylmorpholine hydrochloride (197 mg, 1.32 mmol), 1-(2-chloroethyl)piperidine hydrochloride (243 mg, 1.32 mmol),

Molecular Weight:226.86
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:226.85167
Monoisotopic Mass:224.85372
Topological Polar Surface Area:41.6
Heavy Atom Count:7
Complexity:68
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes