Reaction #64325

Reaction equation

1 -hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone

2-aminoethanethiol

p-toluenesulfonic acid

→

1-Hexyl-3-(2-thiazolidinyl)-4-methoxy-6-methyl-2(1H)-quinolinone

Solvents

methylene chloride

Conditions

Workup

1. 1
   WashThe mixture was washed with aqueous sodium bicarbonate
2. 2
   Otherdried
3. 3
   Otherevaporated
4. 4
   Othercrystallized from ether-hexane

Procedure

A solution of 1 -hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone (Step (2) of Example 1, 1 g) and 2-aminoethanethiol (0.26 g) in methylene chloride (20 ml) containing p-toluenesulfonic acid (0.1 g) was stirred for 3hrs. The mixture was washed with aqueous sodium bicarbonate, dried, evaporated and then crystallized from ether-hexane to give 1-Hexyl-3-(2-thiazolidinyl)-4-methoxy-6-methyl-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: m/e 360 (M+); NMR (CDCl3): δ3.17 (m, 2H, CH2S), 3.86 (m, 2H, CH2N), 6.0 (d, 1H, S-CH-N).

Source