Methyl iodide → N-methyl-N-(phenylmethoxy)-2-nitrobenzenesulfonamide

HRID 1105758Notes

Reaction equation

HRID 1105758 reaction equation
[C:1]1([CH2:7][O:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:22][N:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9839578N-(Benzyloxy)-2-nitrobenzenesulfonamide

Product 1

HCID 20478825N-methyl-N-(phenylmethoxy)-2-nitrobenzenesulfonamideYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 110.6 g of the product of Example 32, 49.8 g of anhydrous potassium carbonate, 55.8 g of methyliodide and 500 ml of acetone was stirred at ambient temperature for 20 hours. The solvent was evaporated and the residue partitioned between methylene chloride and water. Concentration of the organic extract afforded 88.9 g of N-methyl-N-(phenylmethoxy)-2-nitrobenzenesulfonamide as a yellow oil. [NMR:δ 2.8(s, 3H, NCH3)].

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between methylene chloride and water
  3. extractionConcentration of the organic extract

Sources & evidence

ORD record
ord-a91be5917b3d4f65bd0eddeb88820851
Source dataset
uspto-grants-1982_01
Patent number
US04310346

Reaction notes

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