Methyl iodide → HCID 58521914, compound

HRID 2390187Notes

Reaction equation

HRID 2390187 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([Br:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:19]>CN(C=O)C>[Br:15][C:10]1[CH:9]=[C:8]([S:5]([N:4]([CH:1]([CH3:3])[CH3:2])[CH3:19])(=[O:7])=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 7213291N-ISOPROPYL 3-BROMO-4-METHYLBENZENESULFONAMIDE

Product 1

HCID 58521914HCID 58521914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-isopropyl 3-bromo-4-methylbenzenesulfonamide (Combiblocks; 200 mg; 0.68 mmol) in anhydrous DMF (4 mL) was treated with NaH (33 mg; 0.82 mmol) and stirred at RT for five minutes. The resulting mixture was treated with iodomethane (43 μl; 0.68 mmol) and the reaction mixture was stirred for 16 hours. The mixture was treated again with iodomethane (21 μl; 0.34 mmol) and the reaction mixture was stirred at RT for 24 hours. The mixture was quenched with an aqueous (5 N) solution of NaOH and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4, concentrated and purified flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc affording the title compound as a colorless sticky solid.

Workup

  1. stirringthe reaction mixture was stirred for 16 hours
  2. stirringthe reaction mixture was stirred at RT for 24 hours
  3. customThe mixture was quenched with an aqueous (5 N) solution of NaOH
  4. extractionextracted with EtOAc
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified flash column chromatography (silica)
  9. washeluting with cyclohexane containing
  10. temperatureincreasing amounts of EtOAc affording the title compound as a colorless sticky solid

Sources & evidence

ORD record
ord-27839e7cac734f59b34818e5d91dca5b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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