Water → HCID 18509330, compound

HRID 1356635Notes

Reaction equation

HRID 1356635 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[C:6]([C:21]([O:23][CH3:24])=[O:22])[CH:5]=1.S(OC)(O[CH3:29])(=O)=O.O>CN(C=O)C>[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([N:8]([CH3:29])[S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[C:6]([C:21]([O:23][CH3:24])=[O:22])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18509325Methyl 5-chloro-2-[(4-methylbenzene-1-sulfonyl)amino]benzoate

Product 1

HCID 18509330HCID 18509330, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.43 g (10.8 mmol)) in DMF (10.0 ml), 4′-chloro-2′-methoxycarbonyl-p-toluenesulfonanilide (3.33 g (9.80 mmol)) was added under cooling with ice and with stirring. After 15 minutes' stirring under cooling with ice, dimethyl sulfate (1.02 g (10.8 mmol)) was added dropwise, and the reaction mixture was stirred at room temperature for 16 hours. Then, resulting reaction mixture was poured into water and extracted with ethyl acetate, and the extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 2.95 g (85%) of 4′-chloro-2′-methoxycarbonyl-N-methyl-p-toluenesulfonanilide as white crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringAfter 15 minutes' stirring
  4. additionwas added dropwise
  5. stirringthe reaction mixture was stirred at room temperature for 16 hours
  6. customThen, resulting
  7. customreaction mixture
  8. extractionextracted with ethyl acetate
  9. washthe extract was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88af95a476e44708aaa6ddef20507c2c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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