Hydrochloric Acid → HCID 18509230, compound

HRID 1356636Notes

Reaction equation

HRID 1356636 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([C:20]([O:22]C)=[O:21])[CH:3]=1.Cl>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C:20]([OH:22])=[O:21])[C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18509330HCID 18509330, compound

Product 1

HCID 18509230HCID 18509230, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 4′-chloro-2′-methoxycarbonyl-N-methyl-p-toluenesulfonanilide (13.3 g (37.5 mmol)) in methanol (30.0 ml), 10% aqueous sodium hydroxide solution (30.0 ml) was added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 48 hours, and then concentrated under reduced pressure. Water was added to the residue to get a homogeneous solution, followed by addition of concentrated hydrochloric acid (10.0 ml) to bring about precipitation of crystals. To this, ethyl acetate was added to extract the product. The extract was then washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the crystals. The crystals were collected by filtration and washed to give 10.4 g (82%) of the title compound as white crystals.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 48 hours
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. customto get a homogeneous solution
  6. customto bring about precipitation of crystals
  7. additionTo this, ethyl acetate was added
  8. extractionto extract the product
  9. washThe extract was then washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionDiethyl ether was added to the crystals
  13. filtrationThe crystals were collected by filtration
  14. washwashed

Sources & evidence

ORD record
ord-7aca6f5b9741443683e475c2279d7255
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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