반응 #57787

반응 방정식

NH4Cl

2-amino-5-chlorobenzoic acid

nBuLi

N-methyl imidazole

→

product

수율 13.7%

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

수율 13.7%

용매

ether

hexane

반응 조건

후처리

1. 1
   온도refluxed for 1 h
2. 2
   workup.STIRRINGThe reaction mixture was stirred overnight at rt
3. 3
   추출the resulting mixture extracted with ethyl acetate (2×150 ml)
4. 4
   건조The combined organic layers were dried over Na2SO4
5. 5
   기타After removal of solvent
6. 6
   기타the residue was purified by the flash chromatography
7. 7
   기타Crystallization of the product from Et2O/hexane mixture

실험 절차

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.

출처