Water → N-Ethyl-4'-methylthio-2'-nitro-p-toluenesulfonanilide

HRID 1356675Notes

Reaction equation

HRID 1356675 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[C:21]([S:23][CH3:24])[CH:20]=[CH:19][C:7]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([O-:5])=[O:4].[CH2:25](I)[CH3:26].O>CN(C=O)C>[CH2:25]([N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:7]1[CH:19]=[CH:20][C:21]([S:23][CH3:24])=[CH:22][C:6]=1[N+:3]([O-:5])=[O:4])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 185093012'-Nitro-4'-methylthio-p-toluenesulfonanilide

Product 1

HCID 18509310N-Ethyl-4'-methylthio-2'-nitro-p-toluenesulfonanilideYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (65%, 0.21 g (5.76 mmol)) in 4.0 ml of DMF, 2′-nitro-4′-methylthio-p-toluenesulfonanilide (1.50 g (4.43 mmol)) was added with stirring at room temperature. To the resulting mixture, after 30 minutes' stirring at room temperature, ethyl iodide (0.52 ml (6.21 mmol)) was added dropwise and the mixture was stirred at room temperature for 16 hours. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, dilute hydrochloric acid, and saturated aqueous solution of sodium chloride successively. The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was then subjected to silica gel column chromatography with chloroform as eluent to give 1.04 g (64%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 30 minutes' stirring at room temperature
  3. stirringthe mixture was stirred at room temperature for 16 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate, dilute hydrochloric acid, and saturated aqueous solution of sodium chloride successively
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-080e41be164a44c790283355840931f1
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…