Water → HCID 18707361, compound

HRID 263599Notes

Reaction equation

HRID 263599 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][C:25]([CH3:27])=[CH2:26])[C:21]([OH:28])=[C:20]([C:29]([OH:31])=[O:30])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[I-].[K+].O.C(OCC)(=O)C>ClC1C=CC=CC=1Cl.II>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:19]=[C:20]([C:29]([OH:31])=[O:30])[C:21]4[O:28][C:25]([CH3:27])([CH3:26])[CH2:24][C:22]=4[CH:23]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 18707195HCID 18707195, compound

Product 1

HCID 18707361HCID 18707361, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

In 40 ml of o-dichlorobenzene was dissolved, with heating, 2 g of 2-(3,4-diethoxyphenyl)-4-[3-carboxy-4-hydroxy-5-(2-methyl-2-propenyl)phenyl]-thiazole. Thereto were added about 10 mg of iodine and 1.5 g of potassium iodide (ground in-a mortar), and the mixture was refluxed for 14 hours with heating. The reaction mixture was mixed with 30 ml of water and phase separation was conducted. The organic layer was mixed with 30 ml of ethyl acetate. The mixture was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent: dichloromethane) and recrystallized from diisopropyl ether to obtain 1 g of 2-(3,4-diethoxyphenyl)-4-(2,2-dimethyl-7-carboxy-2,3-dihydrobenzofuran-5-yl)thiazole as white powdery crystals.

Workup

  1. temperaturewith heating
  2. temperaturethe mixture was refluxed for 14 hours
  3. temperaturewith heating
  4. washThe mixture was washed with 20 ml of a saturated aqueous sodium chloride solution
  5. customdried
  6. distillationsubjected to distillation
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane)
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-fe749bcacc2a481f9a83de5f33b71245
Source dataset
uspto-grants-1997_07
Patent number
US05643932

Reaction notes

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