Réaction #55511

Équation de réaction

chloroacetonitrile

2-mercaptonicotinic acid

potassium bicarbonate

potassium iodide

dimethylformamide

sodium chloride

→

cyanomethyl 2-(cyanomethylthio)nicotinate

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.WAIT, then at 25° for 15 hr
2. 2
   Filtrationfiltered
3. 3
   workup.DISSOLUTIONThe resulting solid was dissolved in methylene chloride
4. 4
   Séchagedried with magnesium sulfate
5. 5
   Autreevaporated

Mode opératoire

12 Grams (0.16 mole) of chloroacetonitrile was added to a stirred suspension of 6.2 g (0.04 mole) of 2-mercaptonicotinic acid, 8.0 g (0.08 mole) of potassium bicarbonate, and 20 g (0.12 mole) of potassium iodide in 100 ml of dimethylformamide at 10° under nitrogen. The reaction was stirred at 10° for 7 hr., then at 25° for 15 hr. The reaction mixture was then poured into water, saturated with sodium chloride and filtered. The resulting solid was dissolved in methylene chloride, dried with magnesium sulfate and evaporated to give 7.5 g of cyanomethyl 2-(cyanomethylthio)nicotinate. m.p. 140°-143° C. NMR (DMSO) δ3.3(s,2); 4.3(s,2); 6.4(dd,1); 7.4(dd,1); 7.8(dd,1).

Source