2-(4-METHOXY-PHENYL)-THIAZOLIDINE synthesis
- Product Name:2-(4-METHOXY-PHENYL)-THIAZOLIDINE
- CAS Number:31404-08-7
- Molecular formula:C10H13NOS
- Molecular Weight:195.28
Yield:31404-08-7 69%
Reaction Conditions:
in ethanol;water at 20; for 18 h;
Steps:
5
To a solution of P-METHOXYBENZALDEHYDE (1. 81 g, 13.3 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 18 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 (3X20 ml) to remove excess aldehyde. The aqueous layer was basified by addition of solid sodium carbonate (0.3 g) causing the product to precipitate out of solution. The precipitate was filtered, washed carefully WITH WATER (3X20 ML) and dried in a vacuum desiccator to give 2-(4-METHOXYPHENYL)-1, 3-THIAZOLANE (5) as a white solid (0. 55 g, 69%), mp 94-95° (lit mp, 93-94°). 1H nmr (CDCl3, 300 MHz) 2.51, S, NH; 3.05-3. 20, m, H4,4, 5; 3.64, m, H5 ; 3.80, S, OMe; 5.23, s, H2 ; 6. 87, d (8. 7 Hz), H3', 5 ; 7. 44, d (8. 7), H2', H6'. ESI (+ve) MS m/z 196 (M+H, 100%).
References:
WO2004/89927,2004,A1 Location in patent:Page 56
