Sodium Iodide → HCID 68881545, compound

HRID 1723663Notes

Reaction equation

HRID 1723663 reaction equation
[H-].[Na+].[C:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:19][CH2:20][O:21][CH3:22].[I-].[Na+]>CN(C=O)C>[CH3:22][O:21][CH2:20][CH2:19][N:7]([C:3]([CH3:6])([CH3:4])[CH3:5])[S:8]([C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)(=[O:9])=[O:10]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether2×HCID 7314500HCID 7314500, compound

Product 1

HCID 68881545HCID 68881545, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (71 mg, 1.77 mg) was added to a solution of N-t-butyl-4-iodobenzenesulphonamide (Method 73; 500 mg, 1.47 mmol), in anhydrous DMF (15 ml), under nitrogen at 0° C. The resulting suspension was stirred at 0° C. for 30 minutes. A solution of 1-bromo-2-methoxyethane (167 μl, 1.77 mmol), and sodium iodide (265 mg, 1.77 mmol) in DMF (15 ml) (which had been pre-stirred at ambient temperature for 1 hour), was then added dropwise to the mixture so that the reaction temperature was maintained at 0° C. and the mixture then stirred for 10 minutes. The mixture was allowed to warm to ambient temperature, and then heated at 60° C. for 20 hours and then allowed to cool to ambient temperature. A further solution of 1-bromo-2-methoxyethane (167 μl, 1.77 mmol), and sodium iodide (265 mg, 1.77 mmol), in DMF (15 ml), (pre-stirred at ambient temperature for 1 hour), was then added dropwise and the reaction mixture was heated at 60° C. for a further 20 hours. The mixture was then cooled and solvent removed by evaporation. The residue was dissolved in ether (25 ml), washed with 10% aqueous sodium hydroxide solution (20 ml), water (3×25 ml), and dried. The volatiles were removed by evaporation and the residue purified by flash chromatography on silica gel eluting with DCM to yield the title compound (147 mg, 25%), as a clear oil that crystallised on standing. NMR: 1.23 (s, 9H), 3.24 (s, 3H), 3.48 (s, 4H), 7.57 (d, 2H), 7.94 (d, 2H).

Workup

  1. temperaturewas maintained at 0° C.
  2. stirringthe mixture then stirred for 10 minutes
  3. temperatureto warm to ambient temperature
  4. temperatureheated at 60° C. for 20 hours
  5. temperatureto cool to ambient temperature
  6. temperaturethe reaction mixture was heated at 60° C. for a further 20 hours
  7. temperatureThe mixture was then cooled
  8. customsolvent removed by evaporation
  9. dissolutionThe residue was dissolved in ether (25 ml)
  10. washwashed with 10% aqueous sodium hydroxide solution (20 ml), water (3×25 ml)
  11. customdried
  12. customThe volatiles were removed by evaporation
  13. customthe residue purified by flash chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-1a3a9e8f651248c6892318cabf475054
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

Loading…