반응 #43306

반응 방정식

4-morpholinobenzoic acid

4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole

→

title compound

수율 24.4%

6-(4-Morpholinophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

수율 24.4%

용매

POCl3

반응 조건

후처리

1. 1
   기타excess POCl3 was removed under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   세척washed with saturated NaHCO3
4. 4
   건조The organic layer was dried over anhydrous Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude product was purified by chromatography (80% ethyl acetate/hexane; 1 mL methanol/100 mL of solvent)

실험 절차

A mixture of 4-morpholinobenzoic acid (86 mg, 0.42 mmol) and 4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole (102 mg, 0.36 mmol) was refluxed in POCl3 (5 mL) for 2 h. The reaction mixture was cooled to room temperature and excess POCl3 was removed under vacuum. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by chromatography (80% ethyl acetate/hexane; 1 mL methanol/100 mL of solvent) to give the title compound as a yellow solid (40 mg, 0.088 mmol, 24%). 1H NMR (CDCl3): 7.78 (m, 2H), 7.73 (s, 2H), 6.98 (m, 2H), 4.00 (s, 6H), 3.94 (s, 3H), 3.89 (m, 4H), 3.41 (m, 4H).

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