Methanesulfonic Acid → HCID 59593475, compound

HRID 2261241Notes

Reaction equation

HRID 2261241 reaction equation
CS(O)(=O)=O.[O:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]([NH:10][CH2:11][C:12]#[CH:13])=[O:9]>O1CCOCC1>[CH3:13][C:12]1[O:9][C:8]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:6])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 14985789HCID 14985789, compound2×

Product 1

HCID 59593475HCID 59593475, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methane sulfonic acid (10 g, 104 mmol) was added drop wise to a solution of 2-oxo-2-phenyl-N-prop-2-ynyl-acetamide (Intermediate 1) (2.4 g, 12.83 mmol) in 1,4-dioxane (20 mL). The resultant solution was heated at 90° C. for 66 h. The reaction mixture was cooled and the solvent was removed. The dark residue was partitioned between DCM and water. The DCM fraction was washed with 1 M HCl (2×), satd. sodium hydrogencarbonate solution (aq., 2×), then brine. The solution was dried (Na2SO4) and the solvent was removed to give the crude product. Purification was achieved via column chromatography, eluting with cyclohexane/EtOAc (4:1). This afforded the product as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was removed
  3. customThe dark residue was partitioned between DCM and water
  4. washThe DCM fraction was washed with 1 M HCl (2×)
  5. dry with materialThe solution was dried (Na2SO4)
  6. customthe solvent was removed
  7. customto give the crude product
  8. customPurification
  9. washeluting with cyclohexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-5f12c7b779f74421b2fca968fec97e2e
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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