Water → 3-[5-(Imidazo[1,2-a]pyridin-5-yl)pentyl]thiazolidine-2,4-dione

HRID 357003Notes

Reaction equation

ClCCCCCS[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1.[Na].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].O>CN(C)C=O>[N:16]1[CH:15]=[CH:14][N:13]2[C:8]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:20]3[C:21](=[O:23])[CH2:22][S:18][C:19]3=[O:24])=[CH:9][CH:10]=[CH:11][C:12]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2.22 g (10 mmol) of 5-(5-chloropentylthio)imidazo[1,2-a]pyridine and 1.40 g (10 mmol) of thiazolidine-2,4-dione sodium salt in 30 ml of N,N-dimethylformamide was heated at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate→ethyl acetate/ethanol=10/1) to yield 1.56 g (51.4%, light brown oily substance) of the desired product.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washwashed with water
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent: ethyl acetate→ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record: ord-1e98cee1341a44dd8329c2949aa00392
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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