反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
3-[(4-Amino-5-chloro-2-methoxyphenyl)methyl]-5-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2(3H)-one (3 g, 7.5 mmol) and pyridine (0.68 ml, 8.41 mmol) were dissolved in THF (35 ml) under N2 and cooled to 0° C. Bromoacetyl bromide (0.72 ml, 8.26 mmol) was added dropwise and the reaction mixture stirred for 18 h at 24° C. before being partitioned between ethyl acetate (400 ml) and 0.1N HCl solution (50 ml). The organic phase was washed with saturated NaHCO3 solution and brine, and dried over MgSO4. Active carbon (500 mg) was added and the solution filtered through a plug of Celite. Concentration gave 3.8 g (98%); mp 140-182° C. (dec); IR(KBr, υ=cm-1) 3348, 2972, 1784, 1672, 1594, 1234, 1168, 1066; 1H NMR (300 MHz, DMSO-d6) δ 3.77 (3H, s), 4.15 (2H, s), 4.90 (2H, s), 7.47-7.48 (2H, m), 7.86 (2H, d, J=8.4 Hz), 7.96 (1H, d, J=8.3 Hz), 9.30 (1H, s); MS(ESl)m/z: 520(MH+)
WORKUP
后处理
- custombefore being partitioned between ethyl acetate (400 ml) and 0.1N HCl solution (50 ml)
- washThe organic phase was washed with saturated NaHCO3 solution and brine
- dry with materialdried over MgSO4
- additionActive carbon (500 mg) was added
- filtrationthe solution filtered through a plug of Celite
- concentrationConcentration
- customgave 3.8 g (98%)