Methyl iodide → 5-(Methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid methyl ester

HRID 732514Notes

Reaction equation

HRID 732514 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.IC.[C:25](=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:16]=[C:15]([N:17]([S:18]([CH3:21])(=[O:19])=[O:20])[CH3:25])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 688152395-Methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 688153705-(Methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid methyl ester

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 5-methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid methyl ester (2.09 g, 6.36 mmol), iodomethane (1.35 g, 9.55 mmol), potassium carbonate (1.38 g, 10 mmol), and tetrabutylammonium bromide (206 mg, 0.64 mmol) in DMF (10 mL) at room temperature for 30 min. Dilute with ethyl acetate and wash with 10% aqueous potassium carbonate, 1 N lithium chloride and saturated aqueous sodium chloride. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:dichloromethane) to give the title compound as an oil.

Workup

  1. washwash with 10% aqueous potassium carbonate, 1 N lithium chloride and saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:dichloromethane)

Sources & evidence

ORD record
ord-e77f0b5463704250a0a11ea4f3fd00f8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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