Water → 2'-Nitro-4'-methylthio-p-toluenesulfonanilide

HRID 1356674Notes

Reaction equation

HRID 1356674 reaction equation
[N+:1]([C:4]1[CH:20]=[C:19]([S:21][C:22]#N)[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])([O-:3])=[O:2].[BH4-].[Na+].CI.O>CO>[N+:1]([C:4]1[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:9])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 4311764Sodium borohydrideHCID 185092522'-Nitro-4'-thiocyano-p-toluenesulfonanilide

Product 1

HCID 185093012'-Nitro-4'-methylthio-p-toluenesulfonanilideYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2′-Nitro-4′-thiocyano-p-toluenesulfonanilide (5.0 g (14.3 mmol) in methanol (20 ml), sodium borohydride (2.80 g (66.7 mmol)) was added under cooling with ice and with stirring. After 30 minutes' stirring, to the resulting mixture, methyl iodide (3.67 ml (59.0 mmol)) was added dropwise under cooling with ice and the mixture was then stirred at room temperature for 20 hours. Then, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:4) as eluent. The resulting crystals were recrystallized from ethyl acetate to give 2.27 g (47%) of 2′-nitro-4′-methylthio-p-toluenesulfonanilide as orange crystals.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added dropwise
  3. temperatureunder cooling with ice
  4. stirringthe mixture was then stirred at room temperature for 20 hours
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6715ceead43145bdaed3549a1d8ea711
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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