Methyl iodide → HCID 54485631, compound

HRID 2293507Notes

Reaction equation

HRID 2293507 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 faltered and the solid washed with CHCl3 /MeOH. The combined filtrates were evaporated and the residue was purified by flash chromatography on eluting with 0-5% MeOH/CHCl3. The title compound was isolated as a white solid (4.9 g, 94%): 1H (CDCl3): δ8.08 (d, 2H); 7.48 (d,2H); 4.41 (s, 1H); 3.97 (s, 3H); 3.91 (s, 3H); 2.83 (s, 3H).

Workup

  1. washthe solid washed with CHCl3 /MeOH
  2. customThe combined filtrates were evaporated
  3. customthe residue was purified by flash chromatography
  4. washon eluting with 0-5% MeOH/CHCl3

Sources & evidence

ORD record
ord-7dc530dbab2a4fb8ab76fe7fbcc83c46
Source dataset
uspto-grants-1997_11
Patent number
US05686455

Reaction notes

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