Methyl iodide → 4-bromo-N-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide

HRID 1710391Notes

Reaction equation

HRID 1710391 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]I>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:20])[CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 43396864-bromo-N-(tetrahydrofuran-2-ylmethyl)benzenesulfonamide2×

Product 1

HCID 610599944-bromo-N-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.30 g of 4-bromo-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide (compound D2) are dissolved in 150 ml of dry tetrahydrofuran. 590 mg of sodium hydride (strength 60 wt. % dispersion in mineral oil) are added in portions to the solution. After 15 min, 1.67 ml of methyl iodide are slowly added and the reaction mixture is stirred at room temperature for 20 hours. Subsequently, the suspension is concentrated in vacuo, extracted using 200 ml of ethyl acetate and 100 ml of half-saturated brine (sodium chloride solution). The organic layer is dried using Na2SO4, filtered with suction, and concentrated in vacuo to yield 4.53 g of the title compound as an oil. ESI-MS: 334.2/336.0 (MH+, 100%:98%). TLC: Rf=0.78 (dichloromethane/ethanol 20:1 parts by volume).

Workup

  1. concentrationSubsequently, the suspension is concentrated in vacuo
  2. extractionextracted
  3. customThe organic layer is dried
  4. filtrationfiltered with suction
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24e612b7a5ba47178b070ca2167829fa
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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