Water → 2'-nitro-p-toluenesulfonanilide

HRID 1356667Notes

Reaction equation

HRID 1356667 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.O>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 69462-NitroanilineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 2579692'-nitro-p-toluenesulfonanilideYield 63.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Nitroaniline (2.15 g (15.6 mmol)) was dissolved in 10.0 ml of pyridine. To this, p-toluenesulfonyl chloride (3.55 g (18.6 mmol)) was added with stirring at room temperature. After stirring for 15 hours at room temperature, water (100 ml) was added to the reaction mixture to bring about separation of crystals. The crystals were filtered, washed with water, dried and then subjected to silica gel column chromatography with ethyl acetate-hexane (2:3) as eluent to give 2.88 g (53%) of 2′-nitro-p-toluenesulfonanilide as yellow crystals, and 1.17 g (17%) of N,N-bis(p-toluenesulfonyl)-2′-nitroaniline (Compound No. 39) as pale yellow crystals. Physical Constants of 2′-nitro-p-toluenesulfonanilide

Workup

  1. stirringAfter stirring for 15 hours at room temperature
  2. customto bring about separation of crystals
  3. filtrationThe crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-217f66be7832470eb778cb3fa7768351
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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