Water → 4'-Methoxymethoxy-N-methyl-2'-nitro-p-toluenesulfonanilide

HRID 1356645Notes

Reaction equation

HRID 1356645 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:9]([N+:24]([O-:26])=[O:25])[CH:8]=1.S(OC)(O[CH3:31])(=O)=O.O>CN(C=O)C>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([N:11]([CH3:31])[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[C:9]([N+:24]([O-:26])=[O:25])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 185092944'-Methoxymethoxy-2'-nitro-p-toluenesulfonanilide

Product 1

HCID 185093144'-Methoxymethoxy-N-methyl-2'-nitro-p-toluenesulfonanilideYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.40 g (10.0 mmol)) in 15.0 ml of DMF, 4′-methoxymethoxy-2′-nitro-p-toluenesulfonanilide (3.00 g (8.51 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (1.0 ml (10.6 mmol)) was added and the mixture was stirred for 15 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:2) to give 2.91 g (93%) of the title compound as yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringthe mixture was stirred for 15 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f4f3a197df445de85c0dce07d6f3463
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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