반응 #40720

반응 방정식

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

용매

MeOH CH2Cl2

chloride

반응 조건

후처리

1. 1
   온도The mixture was cooled
2. 2
   세척The organics were washed with water, saturated NaCl
3. 3
   건조dried over Na2SO4
4. 4
   농축concentrated in vacuo
5. 5
   기타as is in the next reaction
6. 6
   온도was refluxed 5 hours
7. 7
   기타The excess phoshoryl chloride was removed under reduced pressure
8. 8
   workup.ADDITIONthe subsequent residue was mixed with crushed ice
9. 9
   여과The solids were filtered
10. 10
    세척washed with water
11. 11
    기타dried in vaciio
12. 12
    기타Purification by reversed-phase HPLC

실험 절차

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).

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