HCID 10447619, compound → 2-(1H-Imidazol-1-yl)-1-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}ethan-1-one

HRID 1722833Notes

Reaction equation

HRID 1722833 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[Na].Cl[CH2:8][C:9]([N:11]1[CH2:15][CH2:14][S:13][CH:12]1[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])=[O:10]>CS(C)=O>[N:1]1([CH2:8][C:9]([N:11]2[CH2:15][CH2:14][S:13][CH:12]2[CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[O:10])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 10447619HCID 10447619, compoundHCID 178507081HCID 178507081, compound

Product 1

HCID 30254562-(1H-Imidazol-1-yl)-1-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}ethan-1-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Imidazolyl sodium (3.58 g) is added to a stirred solution of 3-chloroacetyl-2-(o-methoxyphenoxy)methylthiazolidine (5.8 g) in DMSO (35 ml). After 1 hour the mixture is poured in ice and water (200 ml) and the separated oil is extracted with EtOAc (3×30). The organic phases are collected, washed with water, dried on Na2SO4. After evaporation, the crude residue is purified by filtration on a short column of SiO2 using EtOAc and EtOAc/MeOH 85:15 as the eluent to give 3-(imidazol-1-yl)acetyl-2-(o-methoxyphenoxy)methyl-thiazolidine (5.1 g) as a colourless oil.

Workup

  1. additionAfter 1 hour the mixture is poured in ice
  2. extractionwater (200 ml) and the separated oil is extracted with EtOAc (3×30)
  3. customThe organic phases are collected
  4. washwashed with water
  5. customdried on Na2SO4
  6. customAfter evaporation
  7. filtrationthe crude residue is purified by filtration on a short column of SiO2

Sources & evidence

ORD record
ord-bd6c0031d1894f86a7b5fa30af8cc359
Source dataset
uspto-grants-1989_08
Patent number
US04857643

Reaction notes

Loading…