Methyl iodide → HCID 59731061, compound

HRID 130628Notes

Reaction equation

HRID 130628 reaction equation
[CH3:1][S:2]([C:5]1[C:6]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([F:28])([F:27])([F:26])([F:25])[F:24])[CH:18]=2)=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[H-].[Na+].CI.[C:33]([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][S:2]([C:5]1[C:6]([N:16]([CH3:33])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([F:27])([F:26])([F:28])([F:24])[F:25])[CH:18]=2)=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59731060HCID 59731060, compound

Product 1

HCID 59731061HCID 59731061, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg of methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanyl-phenylamino)benzoate (example 5 c) were dissolved in 2 ml of DMF (anhydrous), 13.5 mg of NaH were added, and the mixture was stirred at RT for 15 minutes. Then 15 μl of CH3I were injected and the mixture was left to stand at RT for 18 h. The reaction mixture was then poured into 10 ml of a saturated aqueous NaHCO3 solution and extracted with 40 ml of EA. The organic phase was subsequently washed with 10 ml of water. Drying over MgSO4 and removal of the solvent in vacuo resulted in 120 mg of a pale yellow foam.

Workup

  1. waitthe mixture was left
  2. waitto stand at RT for 18 h
  3. extractionextracted with 40 ml of EA
  4. washThe organic phase was subsequently washed with 10 ml of water
  5. dry with materialDrying over MgSO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-bc9f5effd8fa41e28380ca4644272d4f
Source dataset
uspto-grants-2008_06
Patent number
US07381841B2

Reaction notes

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