Cysteamine Hydrochloride → 2-(4-Methoxy-phenyl)-thiazolidine

HRID 250505Notes

Reaction equation

HRID 250505 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:12][CH2:13][CH2:14][SH:15]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:12][CH2:13][CH2:14][S:15]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 982722-(4-Methoxy-phenyl)-thiazolidineYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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 (3×20 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 (3×20 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%).

Workup

  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. additionThe aqueous layer was basified by addition of solid sodium carbonate (0.3 g)
  6. customto precipitate out of solution
  7. filtrationThe precipitate was filtered
  8. washwashed carefully with water (3×20 ml)
  9. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-4bcae8a2ec094fb08f80a7d9f0f22970
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

Loading…