Ethanol → HCID 11138604, compound

HRID 2082583Notes

Reaction equation

HRID 2082583 reaction equation
C(O)C.[Cl:4][C:5]1[C:10]([CH3:11])=[C:9](Br)[CH:8]=[C:7]([S:13]([CH3:16])(=[O:15])=[O:14])[C:6]=1[CH3:17].C([O-])(=O)C.[Na+].[H][H]>[Pd].O>[Cl:4][C:5]1[C:6]([CH3:17])=[C:7]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 10859468HCID 10859468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11138604HCID 11138604, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

30 ml of ethanol was added to 1.0 g of the crude 2-chloro-4-bromo-6-methylsulfonyl-m-xylene obtained in Example 2, and 0.1 g of 5% palladium active carbon and 1.0 g of anhydrous sodium acetate were further added thereto. The reactor was sealed, and was substituted with hydrogen, then stirring at room temperature for 7 hours. 30 ml of water was added to the reaction liquor, and was concentrated under reduced pressure. 30 ml of EDC was further added thereto, and the resultant mixture was filtered. The EDC layer was taken out from the filtrate, and was washed with 20 ml of water and then with 10 ml of a saturated aqueous solution of common salt, and was dried over anhydrous sodium sulfate. The EDC layer thus obtained was concentrated under reduced pressure and was dried to a solid to obtain 0.7 g of a crude product of the above-identified aimed compound (purity measured by gas chromatography: 75.6%). The crude product thus obtained was recrystallized by methanol to obtain the above-identified aimed compound.

Workup

  1. additionwere further added
  2. customThe reactor was sealed
  3. concentrationwas concentrated under reduced pressure
  4. addition30 ml of EDC was further added
  5. filtrationthe resultant mixture was filtered
  6. washwas washed with 20 ml of water
  7. dry with materialwith 10 ml of a saturated aqueous solution of common salt, and was dried over anhydrous sodium sulfate
  8. customThe EDC layer thus obtained
  9. concentrationwas concentrated under reduced pressure
  10. customwas dried to a solid
  11. customto obtain 0.7 g of a crude product of the above-identified aimed compound (purity measured by gas chromatography: 75.6%)
  12. customThe crude product thus obtained
  13. customwas recrystallized by methanol

Sources & evidence

ORD record
ord-b1628a3f465f45abbe9a41ee5dc16d1f
Source dataset
uspto-grants-1993_02
Patent number
US05189224

Reaction notes

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