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

HRID 1356644Notes

Reaction equation

HRID 1356644 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 185092024-(Methoxymethoxy)-2-nitroaniline

Product 1

HCID 185092944'-Methoxymethoxy-2'-nitro-p-toluenesulfonanilideYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Methoxymethoxy-2-nitroaniline (7.69 g (38.8 mmol)) was dissolved in 19.0 ml of pyridine. To this, p-toluenesulfonyl chloride (8.14 g (42.7 mmol)) was added with stirring at room temperature and the mixture was stirred at room temperature for 18 hours. Then, water (200.0 ml) was added to the reaction mixture, and the resulting mixture was extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with chloroform-ethanol (100:1) as eluent, to give 9.46 g (63%) of 4′-methoxymethoxy-2′-nitro-p-toluenesulfonanilide as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. extractionthe resulting mixture was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfb1ef98e7014bd8a0ace1985496ddb8
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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