Diethyl Ether → HCID 18509249, compound

HRID 1356639Notes

Reaction equation

HRID 1356639 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]([S:20][CH3:21])[CH:3]=1.O.OO.CC[O:27]CC>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)(=[O:8])=[O:9])=[C:4]([S:20]([CH3:21])=[O:27])[CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 449047Hydrogen peroxide waterHCID 18509298HCID 18509298, compound

Product 1

HCID 18509249HCID 18509249, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4′-chloro-N-methyl-2′-methylthio-p-toluenesulfonanilide (0.35 g (1.02 mmol)) in acetic acid (2.0 ml), 30% hydrogen peroxide water (0.12 g (1.06 mmol)) was added dropwise with stirring at room temperature. The mixture was stirred at 50° C. for 15 minutes to get a homogeneous solution, and then stirring was continued at room temperature for 18 hours. Then, the resulting solution was dissolved in ethyl acetate, washed with aqueous sodium hydroxide solution, and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude crystals. Disopropyl ether was added to these crystals. The crystals were filtered and washed to give 0.27 g (74%) of the title compound as white crystals.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at 50° C. for 15 minutes
  3. customto get a homogeneous solution
  4. stirringstirring
  5. washwashed with aqueous sodium hydroxide solution, and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a crude crystals
  9. filtrationThe crystals were filtered
  10. washwashed

Sources & evidence

ORD record
ord-0a25cb4705834b1d9d5d768fd2b8faf9
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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