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

HRID 357014Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][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]([CH2:6][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 15.59 g (70 mmol) of 5-(5-chloropentyl)imidazo[1,2-a]pyridine and 9.74 g (70 mmol) of oxazolidine-2,4-dione potassium salt in 300 ml of N,N-dimethylformamide, 10.49 g (70 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→ethyl acetate/ethanol=10/1) to yield 11.90 g (59.2%, 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→ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record: ord-466c8fb488524e4287f8b639b447d684
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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