Water → 5-[4-(4-Phenyl-2-thiazolylmethoxy)benzyl]-2,4-thiazolidinedione

HRID 867510Notes

Reaction equation

HRID 867510 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1.O>CN(C=O)C.C(O)(=O)C>[C:25]1([C:23]2[N:24]=[C:20]([CH2:19][O:3][C:4]3[CH:17]=[CH:16][C:7]([CH2:8][CH:9]4[S:13][C:12](=[O:14])[NH:11][C:10]4=[O:15])=[CH:6][CH:5]=3)[S:21][CH:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 225573612-(Chloromethyl)-4-phenyl-1,3-thiazole

Product 1

HCID 143018135-[4-(4-Phenyl-2-thiazolylmethoxy)benzyl]-2,4-thiazolidinedioneYield 49.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% in oil, 1.2 g) was added to a solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (3.4 g) in DMF (30 ml), and the mixture was stirred at room temperature for 30 minutes, followed by dropwise addition of a solution of 2-chloromethyl-4-phenylthiazole (4.4 g) in DMF (20 ml) at room temperature. The mixture was stirred at room temperature for 1 hour and at 60° C. for 1 hour, poured into water, neutralized with acetic acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was then distilled off and the oily residue was subjected to column chromatography using silica gel (100 g). Elution with benzene-acetone (25:1, v/v) gave 5-[4-(4-phenyl-2-thiazolylmethoxy)benzyl]-2,4-thiazolidinedione (2.9 g, 49.2%). Recrystallization from ethanol gave light-yellow crystals. M.p. 164°-165° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour and at 60° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was then distilled off
  6. washElution with benzene-acetone (25:1

Sources & evidence

ORD record
ord-f3cedaa1d1aa425aad1ba191c857d411
Source dataset
uspto-grants-1988_10
Patent number
US04775687

Reaction notes

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