反应 #40720

反应方程式

2-(benzo[d][1,3]dioxol-5-yl)acetic acid

thiocarbonohydrazide

thiopene-2-carbonyl chloride

NaHCO3

→

compound 2

3-((benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

溶剂

MeOH CH2Cl2

chloride

反应条件

后处理

1. 1
   温度The mixture was cooled
2. 2
   洗涤The organics were washed with water, saturated NaCl
3. 3
   干燥dried over Na2SO4
4. 4
   浓缩concentrated in vacuo
5. 5
   其他as is in the next reaction
6. 6
   温度was refluxed 5 hours
7. 7
   其他The excess phoshoryl chloride was removed under reduced pressure
8. 8
   workup.ADDITIONthe subsequent residue was mixed with crushed ice
9. 9
   过滤The solids were filtered
10. 10
    洗涤washed with water
11. 11
    其他dried in vaciio
12. 12
    其他Purification by reversed-phase HPLC

实验过程

As shown in FIG. 2, 2-(benzo[d][1,3]dioxol-5-yl)acetic acid (1 mmol) and thiocarbonohydrazide (1.5 mmol) were heated at 170° C. for 15 min. The mixture was cooled and taken up in 5% MeOH/CH2Cl2 and saturated NaHCO3. The organics were washed with water, saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The resulting 5-((benzo[d][1,3]dioxol-5-yl)methyl)-4H-4-amino-3-mercapto-1,2,4-triazole (compound 1001) was used as is in the next reaction. Accordingly, a mixture of compound 1001 and thiopene-2-carbonyl chloride (0.176 g, 1.2 mmol) suspended in excess phoshoryl chloride (˜10 mL) was refluxed 5 hours. The excess phoshoryl chloride was removed under reduced pressure and the subsequent residue was mixed with crushed ice. The solids were filtered, washed with water, and dried in vaciio. Purification by reversed-phase HPLC produced pure 3-((benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (compound 2).

来源