Iodine → HCID 23369684, compound

HRID 1900818Notes

Reaction equation

II.[I-:3].[K+].[CH3:5][C:6](=[CH:22]C)[CH2:7][C:8]1[C:9]([OH:21])=[C:10]2[C:15](=[C:16]([CH3:18])[CH:17]=1)[NH:14][C:13](=[O:19])[C:12]([CH3:20])=[CH:11]2.[C:24](=O)([O-])[O-].[K+].[K+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[I:3][CH2:22][C:6]1([CH3:5])[O:21][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]1[CH3:24])[NH:14][C:13](=[O:19])[C:12]([CH3:20])=[CH:11]3

Participants

Conditions

Temperature: -20 °C

Procedure

Iodine (1.53 g, 6.02 mmol) and potassium iodide (1.01 g, 6.08 mmol) were dissolved in a mixture (105 ml) of chloroform and methanol (4:1), and the resultant mixture was maintained cool. Separately, 6-(2,3-dimethyl-2-propenyl)-5-hydroxy-3,8-dimethylcarbostyril (1.35 g, 5.25 mmol) was dissolved in a mixture (21 ml) of chloroform and methanol (4:1), to which potassium carbonate (1.13, 8.19 mmol) was added. While stirring at -20° C., the above-mentioned cooled solution of iodine and potassium iodide was added thereto, followed by stirring overnight at -20° C. Excessive amounts of aqueous sodium sulfite solution were added to the mixture, followed by stirring at room temperature. Thereafter, extraction was performed with chloroform, and drying and condensing followed. To the resultant pale brown crystals, ethyl acetate was added, which was then ground with heat. After spontaneous cooling, precipitated crystals were collected by filtration to obtain 1.75 g of the title compound (87.0%).

Workup

temperaturecool
additionwas added
stirringby stirring overnight at -20° C
stirringby stirring at room temperature
extractionThereafter, extraction
customdrying
customcondensing
temperatureground with heat
customAfter spontaneous cooling, precipitated crystals
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-6b1c2fb2b95549d494c71912d63c2685
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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