p-Toluenesulfonic acid monohydrate → HCID 70106891, compound

HRID 977239Notes

Reaction equation

HRID 977239 reaction equation
O[CH:2]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[O:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[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:18]=[CH:19][C:20]([CH2:21][CH:22]2[O:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 70107262HCID 70107262, compound

Product 1

HCID 70106891HCID 70106891, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-[4-[1-hydroxy-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]benzyl]-2,4-oxazolidinedione (0.21 g), p-toluenesulfonic acid monohydrate (p-TsOH.H2O) (0.1 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-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl]benzyl]-2,4-oxazolidinedione (0.14 g, 70%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless needles having a melting point of 168°-169° 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-88ee5b19dc6b4675a87dcaa9ddd105bf
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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