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

HRID 1356668Notes

Reaction equation

HRID 1356668 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[CH:21][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].S(OC)(O[CH3:27])(=O)=O.O>CN(C=O)C>[CH3:27][N:8]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:7]1[CH:19]=[CH:20][CH:21]=[CH:22][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 2579692'-nitro-p-toluenesulfonanilide

Product 1

HCID 257978N-methyl-2'-nitro-p-toluenesulfonanilideYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.15 g (3.75 mmol)) in 3.0 ml of DMF, 2′-nitro-p-toluenesulfonanilide (1.00 g (3.42 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (0.4 ml (4.22 mmol)) was added dropwise. After 2 hour's stirring, water was added to bring about separation of crystals. The resulting crystals were filtered, washed with water, dried and subjected to silica gel column chromatography with ethyl acetate-hexane (1:2 to 1:1) as eluent to give 0.93 g (89%) of N-methyl-2′-nitro-p-toluenesulfonanilide (Compound No.38) as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringAfter 2 hour's stirring
  4. customto bring about separation of crystals
  5. filtrationThe resulting crystals were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-049fa4ac107545a8ab950f4aa82cace5
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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