Methyl iodide → Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

HRID 2071118Notes

Reaction equation

HRID 2071118 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:6])=[O:5].I[CH3:23]>CN(C=O)C>[CH3:23][N:7]([C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])[S:4]([CH3:3])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3711983Dimethyl 5-(methylsulfonamido)isophthalate

Product 1

HCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of NaH (0.24 g, 10 mmol, 60% in oil dispersion) in 10 mL of DMF was added dimethyl 5-(methylsulfonamido)isophthalate (1.435 g, 5 mmol) followed by iodomethane (0.62 mL, 10 mmol) at room temperature. After 5 h, the reaction was quenched by H2O (25 mL). Then the reaction mixture was extracted with EtOAc, further washed with H2O to remove excess of DMF, dried over anhydrous Na2SO4 and concentrated. The crude product thus obtained was washed with hexanes to give dimethyl 5-(N-methylmethylsulfonamido)isophthalate as a white solid in 91% (1.37 g) yield.

Workup

  1. customthe reaction was quenched by H2O (25 mL)
  2. extractionThen the reaction mixture was extracted with EtOAc
  3. washfurther washed with H2O
  4. customto remove excess of DMF
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. washwas washed with hexanes

Sources & evidence

ORD record
ord-8d7e507390404a2e8d7badc1f9135198
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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