Methyl iodide → Methyl 3-[(methanesulfonyl)(methyl)amino]-5-nitrobenzoate

HRID 1160448Notes

Reaction equation

HRID 1160448 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:4])=[O:3].CI.[C:21](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:21][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57815097Methyl 3-(methylsulfonamido)-5-nitrobenzoate

Product 1

HCID 57815130Methyl 3-[(methanesulfonyl)(methyl)amino]-5-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 3-[(methylsulfonyl)amino]-5-nitrobenzoate obtained in Reference Example 88.22 g (30 mmol), methyl iodide 2.0 mL (32 mmol), potassium carbonate 10.4 g (75 mmol) and acetone (250 mL) was stirred at room temperature for 16 hours. The mixture was filtered to remove the precipitates and the solvent was evaporated. To the residue was added water (150 mL) and the mixture was extracted twice with ethyl acetate (100 mL). After drying of the mixture on magnesium sulfate, the solvent was evaporated to give 8.55 g (29.7 mmol) of the title compound (yield: 99%).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the
  3. customprecipitates
  4. customthe solvent was evaporated
  5. additionTo the residue was added water (150 mL)
  6. extractionthe mixture was extracted twice with ethyl acetate (100 mL)
  7. customAfter drying of the mixture on magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a2860c02e8c9473eabd8e00f5bc52bf8
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

Loading…