Methyl iodide → 2-[(4-Methoxybenzenesulfonyl)-methylamino]-3-methyl-benzoic acid methyl ester

HRID 583348Notes

Reaction equation

HRID 583348 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[H-].[Na+].I[CH3:27]>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH3:27]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 158592082-(4-Methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester

Product 1

HCID 700522562-[(4-Methoxybenzenesulfonyl)-methylamino]-3-methyl-benzoic acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g (2.985 mmol) of the product of Example 3 in 10 mL of DMF was added 0.149 g (3.731 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 minutes at room temperature and then 0.28 mL (4.478 mmol) of iodomethane was added. The reaction was then stirred for 18 h, and next diluted with ether. The organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo to provide a white solid. The solid was washed with ether/hexanes (1:1) to give 0.788 g (76%) of the desired product as a white solid. Electrospray Mass Spec: 350.1 (M+H).

Workup

  1. stirringThe reaction was then stirred for 18 h
  2. washThe organics were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a white solid
  7. washThe solid was washed with ether/hexanes (1:1)

Sources & evidence

ORD record
ord-2de9a45bc5f641eba2074d0ca50f459b
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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