Sodium Iodide → HCID 21098654, compound

HRID 1351303Notes

Reaction equation

HRID 1351303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[CH:18]=[C:17]([Cl:19])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:31][O:32][CH2:33]Cl.[I-].[Na+]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:21][CH2:31][O:32][CH3:33])[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[CH:18]=[C:17]([Cl:19])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7864Chloromethyl Methyl Ether2×HCID 81531Diisopropylethylamine2×HCID 91325747HCID 91325747, compound

Product 1

HCID 21098654HCID 21098654, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chlorothiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 83) (1.33 g) in dichloromethane (7 mL) was added dropwise diisopropylethylamine (1.2 mL) and 0.34 mL of chloromethyl methyl ether (0.34 mL) on an ice bath. Sodium iodide (25 mg) was added, and the solution was stirred at room temperature for 4 hours at room temperature. In addition, diisopropylethylamine (1.2 mL) and chloromethyl methyl ether (0.34 mL) were added to this solution, and the solution was further stirred for 17 hours. After the solution was diluted with ethyl acetate, and was washed with water and saturated sodium chloride water. After drying the organic layer with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (646 mg) was obtained as a colorless solid. Recovery of raw materials was 557 mg.

Workup

  1. stirringthe solution was further stirred for 17 hours
  2. washwas washed with water and saturated sodium chloride water
  3. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  4. customthe residue that was obtained
  5. customupon removing the solvent
  6. customby evaporation
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-186374bb6b8b424f89856cfe3b2dc01d
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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