Potassium Iodide → HCID 86649446, compound

HRID 389036Notes

Reaction equation

HRID 389036 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[NH:8]1[CH2:13][CH2:12][C:11](=[C:14]2[C:23]3[CH:24]=[C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][C:22]=3[O:21][CH2:20][C:19]3[CH:18]=[CH:17][S:16][C:15]2=3)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[O:7]=[C:5]([CH3:6])[CH2:4][CH2:3][CH2:2][N:8]1[CH2:13][CH2:12][C:11](=[C:14]2[C:23]3[CH:24]=[C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][C:22]=3[O:21][CH2:20][C:19]3[CH:18]=[CH:17][S:16][C:15]2=3)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 799932-Pentanone, 5-chloro-HCID 86649447HCID 86649447, compound

Product 1

HCID 86649446HCID 86649446, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-Chloro-2-pentanone (2.4 mL, 20.9 mmol) was added to a DMF (50 mL) solution of methyl (4-piperidin-4-ylidene-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate (2.50 g, 7.0 mmol), anhydrous potassium carbonate (2.15 g, 15.6 mmol), and potassium iodide (1.41 g, 8.5 mmol), and the mixture was stirred overnight at 80° C. The solvents were distilled off under a reduced pressure, water was added to the residue, and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvents were then distilled off under a reduced pressure. The residue was purified by column chromatography (chloroform:methanol=19:1), to give 2.40 g (78%) of the captioned compound in the form of an oily product.

Workup

  1. distillationThe solvents were distilled off under a reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvents were then distilled off under a reduced pressure
  6. customThe residue was purified by column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-630c1e63cf3a45978542233569afccdc
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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