HCID 10447619, compound → 2-(1H-Imidazol-1-yl)-1-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}ethan-1-one
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]1Participants
4
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.