Imidazole → HCID 54250108, compound

HRID 905082Notes

Reaction equation

HRID 905082 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[I-].[Na+].[C:8]([O:16][CH2:17][C@@H:18]1[O:23][C@@H:22]([O:24][CH:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH2:26]Br)[CH2:21][CH2:20][CH2:19]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C)C=O>[C:8]([O:16][CH2:17][C@@H:18]1[O:23][C@@H:22]([O:24][CH:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH2:26][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:21][CH2:20][CH2:19]1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 5238Sodium IodideHCID 54034610HCID 54034610, compound

Product 1

HCID 54250108HCID 54250108, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

8.24 g of imidazole and 12.0 g of sodium iodide were added to a solution of 19.70 g of trans-6-benzoyloxymethyl-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran in 150 ml of dimethylformamide, and the resulting mixture was stirred on an oil bath at 130° C. for 6.5 hours. The reaction mixture was then cooled, poured into water and extracted with diethyl ether. The ethereal extract was washed with aqueous sodium chloride and dried over anhydrous sodium sulphate, after which the solvent was evaporated off. The residue was purified by column chromatography through silica gel eluted with a B 100:25:1 by volume mixture of ethyl acetate, benzene and triethylamine, to give 9.25 g of the title compound as a liquid.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with diethyl ether
  3. extractionThe ethereal extract
  4. washwas washed with aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. customafter which the solvent was evaporated off
  7. customThe residue was purified by column chromatography through silica gel
  8. washeluted with a B 100:25:1 by volume mixture of ethyl acetate, benzene and triethylamine

Sources & evidence

ORD record
ord-44d5fcefcc6742e5ba06aebdf8a9086e
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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