p-Toluenesulfonic acid monohydrate → HCID 67707055, compound

HRID 977237Notes

Reaction equation

HRID 977237 reaction equation
O[CH:2]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]2[O:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:19][CH:18]=1)[CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][CH:3]=[CH:2][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]2[O:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 70109253HCID 70109253, compound

Product 1

HCID 67707055HCID 67707055, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-[2-[4-[1-hydroxy-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]phenyl]ethyl]-2,4-oxazolidinedione (0.32 g), p-toluenesulfonic acid monohydrate (p-TsOH.H2O) (0.145 g) and toluene (40 ml) was stirred under refluxing conditions for 2 hours. The reaction mixture was washed with an aqueous solution of sodium hydrogen carbonate and water, dried (MgSO4) and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography. From the fraction eluted with chloroform-methanol (100:2), 5-[2-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl]phenyl]ethyl]-2,4-oxazolidinedione (0.235 g, 77%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless needles having a melting point of 175°-176° C.

Workup

  1. washThe reaction mixture was washed with an aqueous solution of sodium hydrogen carbonate and water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washFrom the fraction eluted with chloroform-methanol (100:2)

Sources & evidence

ORD record
ord-c66018fd264c4b7fb9aa3f248807c34d
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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