Methanesulfonic Acid → HCID 54718246, compound

HRID 1721387Notes

Reaction equation

HRID 1721387 reaction equation
C(N(CC)[C:4](=[O:26])[CH:5]([CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6](=[O:15])[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[OH:14])C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[Cl:13][C:11]1[CH:10]=[CH:9][C:8]2[O:14][C:4](=[O:26])[C:5]([CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:6]([OH:15])[C:7]=2[CH:12]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22415005HCID 22415005, compound

Product 1

HCID 54718246HCID 54718246, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N,N-diethyl-2-hydroxy-5-chloro-β-oxo-α-(3-phenoxypropyl)benzenepropanamide (0.25 g; 6.6 mmol) (prepared in Example I) in toluene (5 ml) was added methanesulfonic acid (0.07 g; 0.7 mmol). The resulting mixture was heated to reflux and stirred for 20 minutes. The mixture was cooled and the solvent removed under reduced pressure. The residue was dissolved in a 1:1 mixture of EtOAc/Et2O (10 ml), washed with saturated aqueous NaCl, and dried (MgSO4). The solvent was removed in vacuo to provide an oil which crystallized from Et2O to provide 0.16 g (83% yield) of the title compound, m.p. 162°-163° C. NMR (DMSO-d6) δ1.90 (m, 2H), 2.68 (t, 2H), 3.99 (t, 2H), 6.91 (m, 3H), 7.26 (m, 2H), 7.41 (d, 1H), 7.63 (dd, 1H), 7.95 (d, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in a 1:1 mixture of EtOAc/Et2O (10 ml)
  6. washwashed with saturated aqueous NaCl
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto provide an oil which
  10. customcrystallized from Et2O

Sources & evidence

ORD record
ord-68e18cff3940430293b194c1e2652007
Source dataset
uspto-grants-1996_04
Patent number
US05510375

Reaction notes

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