Sodium hydride → 2,4-Thiazolidinedione, 5-[[4-[2-(1,3-dioxolan-2-yl)ethoxy]phenyl]methyl]-

HRID 1953748Notes

Reaction equation

HRID 1953748 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1>CN(C)C=O>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[CH2:20][CH2:19][O:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

Product 1

HCID 106873642,4-Thiazolidinedione, 5-[[4-[2-(1,3-dioxolan-2-yl)ethoxy]phenyl]methyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 15.0 g of 5-(4-hydroxy-benzyl)thiazolidine-2,4-dione, 8.80 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 17 ml of 2-(2-bromoethyl)-1,3-dioxolane and 80 ml of dimethylformamide were used, and that the product was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 6.67 g of the title compound, melting at 102-104° C.

Workup

  1. customA procedure similar to that described in Preparation 46
  2. customthat the product was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-70bef347194e4f5f9362450a39ccafc7
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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