Water → N-(2,4-Dinitrophenyl)-N-ethyl-4-methylbenzene-1-sulfonamide

HRID 1356625Notes

Reaction equation

HRID 1356625 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[NH:8][CH2:9][CH3:10])([O-:5])=[O:4].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[N:8]([CH2:9][CH3:10])[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 77454N-Ethyl-2,4-dinitroaniline

Product 1

HCID 18509204N-(2,4-Dinitrophenyl)-N-ethyl-4-methylbenzene-1-sulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.12 g (3.00 mmol)) in DMF (4.0 ml), 2,4-dinitro-N-ethylaniline (0.42 g (1.99 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, p-toluenesulfonyl chloride (0.57 g (2.99 mmol)) was added. After two hours' stirring at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography with ethyl acetate-hexane (1:2) as eluent, to give 0.47 g (65%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringAfter two hours' stirring at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated sodium chloride solution
  6. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8ef0eca9de543be8a86a54ea52f84e3
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…