Methyl iodide → HCID 54485631, compound

HRID 479773Notes

Reaction equation

HRID 479773 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:17]([O-])([O-])=O.[K+].[K+].CI>CO>[CH3:17][N:5]([CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18771474HCID 18771474, compound

Product 1

HCID 54485631HCID 54485631, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 4-[(methanesulfonamido)methyl]benzoate (5 g, 20.6 mmol) in MeOH (100 mL) at rt was added K2CO3 (2.9 g, 21 mmol). Methyl iodide (7 ml, 16 g, 112 mmol) was added and the mixture stirred overnight. The reaction was filtered and the solid washed with CHCl3/MeOH. The combined filtrates were evaporated and the residue was purified by flash chromatographyon eluting with 0-5% MeOH/CHCl3. The title compound was isolated as a white solid (4.9 g, 94%): 1H (CDCl3): d 8 .08 (d, 2H); 7.48 (d,2H); 4.41 (s, 1H); 3.97 (s, 3H); 3.91 (s, 3H); 2.83 (s, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. washthe solid washed with CHCl3/MeOH
  3. customThe combined filtrates were evaporated
  4. customthe residue was purified by flash chromatographyon
  5. washeluting with 0-5% MeOH/CHCl3

Sources & evidence

ORD record
ord-c8b76404c1ae4f189ec48c972ee3dd19
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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