反応 #813420

反応方程式

CaCl2

thionyl chloride

p-nitrophenol

trans-urocanic acid

→

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

反応条件

後処理

1. 1
   その他equipped with a drying tube
2. 2
   その他is progressively brought to 140° C
3. 3
   抽出A brown powder is extracted with CHCl3 / MeOH (150 ml, 2:1)
4. 4
   温度while heating
5. 5
   その他The undissolved material is separated by filtration
6. 6
   workup.ADDITIONthe filtrate is treated with active charcoal
7. 7
   濃縮Concentration
8. 8
   workup.ADDITIONis added so as
9. 9
   その他precipitation of a solid (1.96 g; overall crude yield: 61%)
10. 10
    その他The latter is recrystallized from MeOH
11. 11
    洗浄the product is washed with diethyl ether in order
12. 12
    その他to remove any trace of p-nitrophenol
13. 13
    その他giving a crystalline white solid, M.p. 220°-222° C.

実験手順

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.

出典