Reaction #43306

Reaction equation

4-morpholinobenzoic acid

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

→

title compound

Yield 24.4%

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

Yield 24.4%

Solvents

POCl3

Conditions

Workup

1. 1
   Otherexcess POCl3 was removed under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Washwashed with saturated NaHCO3
4. 4
   DryingThe organic layer was dried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude product was purified by chromatography (80% ethyl acetate/hexane; 1 mL methanol/100 mL of solvent)

Procedure

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).

Source