反応 #40720

反応方程式

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

溶媒

MeOH CH2Cl2

chloride

反応条件

後処理

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

実験手順

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).

出典