반응 #813420

반응 방정식

CaCl2

thionyl chloride

p-nitrophenol

trans-urocanic acid

→

p-Nitrophenyl trans-3-(1H-imidazol-4-yl)-2-propenoate

반응 조건

후처리

1. 1
   기타equipped with a drying tube
2. 2
   기타is progressively brought to 140° C
3. 3
   추출A brown powder is extracted with CHCl3 / MeOH (150 ml, 2:1)
4. 4
   온도while heating
5. 5
   기타The undissolved material is separated by filtration
6. 6
   workup.ADDITIONthe filtrate is treated with active charcoal
7. 7
   농축Concentration
8. 8
   workup.ADDITIONis added so as
9. 9
   기타precipitation of a solid (1.96 g; overall crude yield: 61%)
10. 10
    기타The latter is recrystallized from MeOH
11. 11
    세척the product is washed with diethyl ether in order
12. 12
    기타to remove any trace of p-nitrophenol
13. 13
    기타giving a crystalline white solid, M.p. 220°-222° C.

실험 절차

2 ml (27.5 mmol) of freshly distilled thionyl chloride are added to a finely ground mixture of 1.51 g (10.8 mmol) of p-nitrophenol and 1.5 g (10.8 mmol) of trans-urocanic acid in a round-bottomed flask equipped with a drying tube containing CaCl2. The mixture is progressively brought to 140° C. After 4 h, the mixture is slowly cooled to room temperature. A brown powder is extracted with CHCl3 / MeOH (150 ml, 2:1) while heating. The undissolved material is separated by filtration and the filtrate is treated with active charcoal. Concentration is carried out under vacuum and diethyl ether is added so as to induce precipitation of a solid (1.96 g; overall crude yield: 61%). The latter is recrystallized from MeOH and the product is washed with diethyl ether in order to remove any trace of p-nitrophenol, giving a crystalline white solid, M.p. 220°-222° C.

출처