반응 #161642

반응 방정식

potassium phosphate

4-imidazol-1-yl-phenyl amine

ethanol

ethyl pyruvate

→

2-[(E)-4-imidazol-1-yl-phenylimino]-propionic acid ethyl ester

용매

hydrochloric acid MeOH

반응 조건

후처리

1. 1
   농축this was concentrated under reduced pressure
2. 2
   workup.ADDITIONan aqueous solution of sodium nitrite (304 mg, 2.5 ml) was added dropwise
3. 3
   workup.ADDITIONThe reaction mixture was slowly added dropwise to an aqueous solution
4. 4
   기타prepared in advance from aqueous solutions of sodium hydrosulfite (2.3 g, 13 ml) and 5 M sodium hydroxide (400 μl)
5. 5
   기타at 5° C.
6. 6
   workup.STIRRINGAfter stirring at 50° C. for 30 minutes
7. 7
   workup.STIRRINGthe mixture was further stirred at 25° C. for 10 hours
8. 8
   여과The resulting precipitate was collected by filtration
9. 9
   기타dried

실험 절차

4-imidazol-1-yl-phenyl amine (637 mg) was dissolved in 2 M hydrochloric acid/MeOH (3 ml), and this was concentrated under reduced pressure. The residue was suspended in concentrated hydrochloric acid (1 ml), and an aqueous solution of sodium nitrite (304 mg, 2.5 ml) was added dropwise thereto over 30 minutes at 0° C. on ice. The reaction mixture was slowly added dropwise to an aqueous solution prepared in advance from aqueous solutions of sodium hydrosulfite (2.3 g, 13 ml) and 5 M sodium hydroxide (400 μl), while keeping the temperature of the reaction mixture at 5° C. or lower. Then, the mixture was stirred at 25° C. for one hour. An ethanol solution (5 ml) of ethyl pyruvate (465 μl) was added dropwise to the reaction mixture. After stirring at 50° C. for 30 minutes, the mixture was further stirred at 25° C. for 10 hours. The pH of the mixture was adjusted to 11 using an aqueous solution (about 10 ml) of 20% potassium phosphate. The resulting precipitate was collected by filtration, and dried. Thus, 2-[(E)-4-imidazol-1-yl-phenylimino]-propionic acid ethyl ester was obtained as a pale yellow powder (1.1 g, 99%).

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