Reaction #83170

Reaction equation

3-benzyloxy-4-carboxy-1-methyl-2(1H)-pyridinone

2-mercaptothiazoline

N,N'-dicyclohexylcarbodiimide

→

title compound

Yield 80.4%

3-benzyloxy-1-methyl-4-(2-thioxothiazolidin-1-yl)carbonyl-2(1H)-pyridinone

Yield 80.4%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherthe dicyclohexylurea (DCU) solids are removed by filtration
2. 2
   Otherthe yellow filtrate is rotary evaporated
3. 3
   Otherto give a yellow solid
4. 4
   OtherCrystallization from isopropanol-methylene chloride

Procedure

To a solution of 3-benzyloxy-4-carboxy-1-methyl-2(1H)-pyridinone (1.05 g, 4 mmol), 2-mercaptothiazoline (0.50 g, 4.2 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) in dry methylene chloride (50 mL), N,N'-dicyclohexylcarbodiimide (DCC) (0.86 g, 4.2 mmol) is added. Alter stirring for 4 hours, the dicyclohexylurea (DCU) solids are removed by filtration, the yellow filtrate is rotary evaporated to give a yellow solid. Crystallization from isopropanol-methylene chloride gives the title compound (1.16 g, 80.4%) as bright yellow crystalline plates, m.p. 149°-150° C. 1H NMR (250 MHz, CDCl3) δ2.867 (t, 2H, J=7.32), 3.594 (s, 3H), 4.313 (t, 2H, J=7.33), 5.301 (s, 2H), 6.107 (d, 1H, J=6.99), 7.126 (d, 1H, J=7.00), 7.31-7.45 (m, 5H). Anal for C17H16N2O3S2Calcd. (found): C, 56.64 (56.36); H, 4.47 (4.47); N, 7.73 (7.73); S, 17.78 (17.41).

Source