Ethylene Glycol → HCID 58516136, compound

HRID 1945234Notes

Reaction equation

HRID 1945234 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])=[C:4](I)[CH:3]=1.Cl.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[SH:29])[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([S:29][C:27]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:28]=2[N:19]=[CH:20][CH:21]=[CH:22]3)[CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 3082386Quinoline-8-thiol hydrochlorideHCID 86034392HCID 86034392, compound

Product 1

HCID 58516136HCID 58516136, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from step (i) (0.262 g), 8-quinolinethiol hydrochloride (0.141 g), copper (I) iodide (7 mg), potassium carbonate (0.295 g) and ethylene glycol (0.08 ml) in iso-propanol (3 ml) was heated at 80° C. for 48 h. The mixture was partitioned between DCM/2M hydrochloric acid, the organics dried, evaporated under reduced pressure and the residue purified by chromatography on silica eluting with DCM:methanol:acetic acid (90:9:1). The residue was triturated with diethylether/methanol, filtered and dried, yield 0.101 g.

Workup

  1. customThe mixture was partitioned between DCM/2M hydrochloric acid
  2. customthe organics dried, evaporated under reduced pressure
  3. customthe residue purified by chromatography on silica eluting with DCM:methanol:acetic acid (90:9:1)
  4. customThe residue was triturated with diethylether/methanol
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-21d41ea1545a4be8a7f845b5b6e4f36d
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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