反应 #57787

反应方程式

NH4Cl

2-amino-5-chlorobenzoic acid

nBuLi

N-methyl imidazole

→

product

收率 13.7%

(2-Amino-5-chloro-phenyl)-(1-methyl-1H-imidazol-2-yl)-methanone

收率 13.7%

溶剂

ether

hexane

反应条件

后处理

1. 1
   温度refluxed for 1 h
2. 2
   workup.STIRRINGThe reaction mixture was stirred overnight at rt
3. 3
   萃取the resulting mixture extracted with ethyl acetate (2×150 ml)
4. 4
   干燥The combined organic layers were dried over Na2SO4
5. 5
   其他After removal of solvent
6. 6
   其他the residue was purified by the flash chromatography
7. 7
   其他Crystallization of the product from Et2O/hexane mixture

实验过程

To a solution of nBuLi (0.0730 mol) in hexane was added N-methyl imidazole (0.0608 mol) drop wise at -40° C. over 30 min under a nitrogen atmosphere. The resulting yellow solution was stirred for a further 3 hr at rt, and then refluxed for 1 h. 2-amino-5-chlorobenzoic acid (1.74 g, 0.01014 mole) in dry ether (60 ml) was then added to the reaction mixture. The reaction mixture was stirred overnight at rt. To the reaction mixture was added saturated NH4Cl solution and the resulting mixture extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over Na2SO4. After removal of solvent, the residue was purified by the flash chromatography using ethyl acetate/hexane (1:4) as eluent. Crystallization of the product from Et2O/hexane mixture gave 300 mg (13.7%) of product as yellow solid.

来源