Isopropanol → HCID 67292391, compound

HRID 1685405Notes

Reaction equation

HRID 1685405 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(O)(C)C.[SH:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>C(OCC)(=O)C.[Cu]I.COCCOC>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([S:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[N:13][CH:12]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 5850584-ThiobenzonitrileHCID 110639836-iodopyridin-3-ol

Product 1

HCID 67292391HCID 67292391, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

0.25 g (1.31 mM) of copper(I) iodide, 7.26 g (52.5 mM) of potassium carbonate and 5.8 g (26.25 mM) of 6-iodo-3-pyridinol are introduced into a tube under an argon atmosphere. 30 ml of isopropanol, 5 g of 1,2-dimethoxyethane and 3.55 g (26.25 mM) of 4-mercaptobenzonitrile are then added. The tube is sealed and heated at 80° C. for 24 hours. When the mixture has returned to room temperature, it is diluted with 120 ml of ethyl acetate and filtered, the solid on the filter is washed with ethyl acetate and the organic phases are concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: cyclohexanol/ethyl acetate 55/45; v/v) to give the expected product in the form of a beige powder with a yield of 53%.

Workup

  1. customThe tube is sealed
  2. customhas returned to room temperature
  3. filtrationfiltered
  4. washthe solid on the filter is washed with ethyl acetate
  5. concentrationthe organic phases are concentrated under reduced pressure
  6. customThe evaporation residue is purified by chromatography on a silica column (eluent

Sources & evidence

ORD record
ord-d35b8f0e46a14c3e91c0781a5f88e222
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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