Hydrochloric Acid → HCID 19045450, compound

HRID 1781401Notes

Reaction equation

HRID 1781401 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].Cl[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:19])=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=1.Cl>CS(C)=O>[OH:19][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[CH:15][C:14]=1[C:16](=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 22557013HCID 22557013, compound

Product 1

HCID 19045450HCID 19045450, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a mixture of sodium hydride (60% dispersion in mineral oil, 1.60 g, 40.0 mmol) in 25 mL DMSO under Argon was added dropwise a solution of methanesulfonamide (3.80 g, 40.0 mmol) in 10 mL DMSO. The resulting mixture was stirred 30 minutes and a solution of 5'-(chloromethyl)-2'-hydroxyacetophenone (3.69 g, 20.0 mmol) in 10 mL DMSO was added. The resulting mixture was stirred three hours, poured into 150 mL ice water, acidified with 14 mL 3N hydrochloric acid, and the mixture extracted with methylene chloride (3×200 mL). The extract was washed with water (50 mL) and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated in vacuo to give an oil which was partially purified by flash chromatography eluting with 3:97 methanol:chloroform to give a gum. The gum was stirred under 25 mL water to remove residual DMSO, the aqueous supernatant.was decanted, and the residue was dried in vacuo. The resulting material was crystallized from ethylacetate to remove 0.67 g of a by-product identified as N,N-bis[(3-acetyl-4-hydroxyphenyl)methyl]methanesulfonamide. The mother liquor was concentrated in vacuo to give a residue which was re-chromatography to give a solid. The solid was recrystallized from n-butylchloride to give 0.60 g (12%) product, as a white solid, mp 85°-86.5° C.

Workup

  1. stirringThe resulting mixture was stirred three hours
  2. extractionthe mixture extracted with methylene chloride (3×200 mL)
  3. washThe extract was washed with water (50 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an oil which
  8. customwas partially purified by flash chromatography
  9. washeluting with 3:97 methanol
  10. customchloroform to give a gum
  11. stirringThe gum was stirred under 25 mL water
  12. customto remove residual DMSO
  13. customthe aqueous supernatant.was decanted
  14. customthe residue was dried in vacuo
  15. customThe resulting material was crystallized from ethylacetate
  16. customto remove 0.67 g of a by-product
  17. concentrationThe mother liquor was concentrated in vacuo
  18. customto give a residue which
  19. customto give a solid
  20. customThe solid was recrystallized from n-butylchloride

Sources & evidence

ORD record
ord-58e4f6ee25724c079c75ffc776570d5f
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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