Réaction #47381

Équation de réaction

5-(4-methoxy-benzyl)-[1,3,4]oxathiazol-2-one

4-toluenesulfonylcyanide

→

3-(4-methoxy-benzyl)-5-(toluene-4-sulfonyl)-[1,2,4]thiadiazole

Rendement 86.0%

Solvants

mesitylene

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting brown solution was cooled
2. 2
   Autrepurified by flash chromatography (silica gel, 0% to 33% ethyl acetate/hexanes) which

Mode opératoire

To a suspension of 5-(4-methoxy-benzyl)-[1,3,4]oxathiazol-2-one (335 mg, 1.50 mmol) in mesitylene (3 mL) was added 4-toluenesulfonylcyanide (572 mg, 3.00 mmol) and the resulting mixture heated to 150° C. for 135 min. The resulting brown solution was cooled and purified by flash chromatography (silica gel, 0% to 33% ethyl acetate/hexanes) which afforded 3-(4-methoxy-benzyl)-5-(toluene-4-sulfonyl)-[1,2,4]thiadiazole (462 mg, 86%) as a dark yellow solid.

Source