Dimethylformamide → 3-Chloro-4-iodo-N,N-dimethylbenzenesulfonamide

HRID 1694743Notes

Reaction equation

HRID 1694743 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11](N)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[I:10].CI.[CH3:17][N:18]([CH:20]=O)C>>[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([N:18]([CH3:20])[CH3:17])(=[O:12])=[O:13])[CH:7]=[CH:8][C:9]=1[I:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 672810493-Chloro-4-iodobenzenesulfonamide

Product 1

HCID 672802043-Chloro-4-iodo-N,N-dimethylbenzenesulfonamide

Procedure

Sodium hydride (0.33 g) was added to a solution of the product from step (i) (1.2 g) in DMF (25 ml) and stirred for 20 min. Methyl iodide (0.5 ml) was added dropwise and then stirred for a further 1 h. The reaction mixture was quenched with water, extracted with EtOAc, dried (MgSO4) and evaporated. The residue was treated with ether to give to give the subtitle compound as a white solid. Yield 0.45 g.

Workup

  1. stirringstirred for a further 1 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. additionThe residue was treated with ether
  7. customto give

Sources & evidence

ORD record
ord-8e940acfa8d143c38dcbfcb1a59be9ad
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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