N-bromobutanimide → 5-Butylidene-3-[4-(3-bromoimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357153Notes

Reaction equation

[CH:1](=[C:5]1[S:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[N:21]3[CH:22]=[CH:23][N:24]=[C:20]3[CH:19]=[CH:18][CH:17]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].[Br:26]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)(Cl)Cl>[CH:1](=[C:5]1[S:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[N:21]3[C:22]([Br:26])=[CH:23][N:24]=[C:20]3[CH:19]=[CH:18][CH:17]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.13 g (3.0 mmol) of 5-butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione in 15 ml of carbon tetrachloride, 0.59 g (3.3 mmol) of N-bromosuccinimide was added at room temperature, followed by stirring at 80° C. for 90 minutes. After the reaction mixture was cooled, saturated aqueous sodium hydrogen carbonate was added. The organic layer was separated and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1→1/4) to yield 1.11 g (81.4%, yellow oily substance) of the desired product.

Workup

temperatureAfter the reaction mixture was cooled
customThe organic layer was separated
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1→1/4)

Sources & evidence

ORD record: ord-ac94fe490bc74d89a74132bc04a9d4e5
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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