تفاعل #57787

معادلة التفاعل

NH4Cl

2-amino-5-chlorobenzoic acid

nBuLi

N-methyl imidazole

→

product

المردود 13.7%

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

المردود 13.7%

المذيبات

ether

hexane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 1 h
2. 2
   workup.STIRRINGThe reaction mixture was stirred overnight at rt
3. 3
   استخلاصthe resulting mixture extracted with ethyl acetate (2×150 ml)
4. 4
   تجفيفThe combined organic layers were dried over Na2SO4
5. 5
   أخرىAfter removal of solvent
6. 6
   أخرىthe residue was purified by the flash chromatography
7. 7
   أخرىCrystallization of the product from Et2O/hexane mixture

الإجراء التجريبي

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.

المصدر