Veratraldehyde → 2-(3,4-Dimethoxyphenyl)-1,3-thiazolidine

To a solution of 3,4-dimethoxybenzaldehyde (2.19 g, 13.2 mmol) in ethanol (15 ml) was added dropwise a solution of cysteamine HCl (0.5 g, 4.4 mmol) in water (5 ml) and the solution stirred at RT for 40 h. The bulk of the ethanol was removed by rotary evaporator and the residue was diluted with water (15 ml) and extracted with diethyl ether (3×20 ml) to remove excess aldehyde. The aqueous layer was basified with solid sodium carbonate (0.3 g) resulting in the formation of an oil. The mixture was extracted with ether (2×25 ml), washed with brine (1×50 ml), dried (MgSO4) and evaporated to give a clear oil that solidified on standing (0.77 g). The material was triturated with hexane (3×5 ml) to give 2-(3,4-dimethoxyphenyl)-1,3-thiazolane (8) as a friable white solid (0.65 g, 66%), mp 54-56°.

1. customThe bulk of the ethanol was removed by rotary evaporator
2. additionthe residue was diluted with water (15 ml)
3. extractionextracted with diethyl ether (3×20 ml)
4. customto remove excess aldehyde
5. customresulting in the formation of an oil
6. extractionThe mixture was extracted with ether (2×25 ml)
7. washwashed with brine (1×50 ml)
8. dry with materialdried (MgSO4)
9. customevaporated
10. customto give a clear oil that solidified
11. customThe material was triturated with hexane (3×5 ml)

ORD record

ord-50fd9367caf04a0e902bf45faef21995

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863313B2