Thiazolidinedione → HCID 22342547, compound

HRID 583788Notes

Reaction equation

HRID 583788 reaction equation
[S:1]1CC(=O)[NH:3][C:2]1=[O:7].[H-].[Na+].[Li+].[CH3:11]C([N-]C(C)C)C.CI.C1[CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:11][O:7][C:2]1[S:1][CH:21]=[C:22]([O:23][CH3:24])[N:3]=1

Participants

6

Reactant 5

HCID 5437ThiazolidinedioneHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2724682Lithium diisopropylamide

Product 1

HCID 22342547HCID 22342547, compound

Procedure

To a stirred solution of 2,4-thiazolidindione (0.01 mol) in a solvent such as THF is added from 2 to 4 mol equivalents of a non-nucleophilic base such as sodium hydride or LDA, followed by methyl iodide, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the mixture is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 2,4-dimethoxythiazole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. customReaction progress

Sources & evidence

ORD record
ord-9dc56365222c4a989f4260db0127b25d
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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