Water → 3-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

HRID 357010

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[K].[O:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].[I-].[Na+].O>CN(C)C=O>[N:15]1[CH:14]=[CH:13][N:12]2[C:7]([S:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]3[C:20](=[O:22])[CH2:21][O:17][C:18]3=[O:23])=[CH:8][CH:9]=[CH:10][C:11]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6.30 g (26.2 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 3.64 g (26.2 mmol) of oxazolidine-2,4-dione potassium salt in 100 ml of N,N-dimethylformamide, 3.92 g (26.2 mmol) of sodium iodide was added, followed by stirring at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to yield 5.70 g (71.4%, light orange crystal) of the desired product.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe organic layer was washed with water
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record: ord-27485b8152fb4f81a5a886d5a64aeede
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Linked notes

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