Sulfuric Acid → 5-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione

HRID 4389Notes

Reaction equation

HRID 4389 reaction equation
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[N:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:20][C:21]=3[CH3:22])=[CH:11][CH:10]=2)[S:3]1.[OH:29]S(O)(=O)=O.O1CCOCC1>O>[CH3:22][C:21]1[O:20][C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:18][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:29])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 140348400HCID 140348400, compound

Product 1

HCID 137138985-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedioneYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone (11.4 g), 1N.H2SO4 (100 ml) and dioxane (100 ml) was stirred at 80° C. for 5 hours, and poured in water. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (200 g), and from the fractions eluted with chlorform-methanol (100:1, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (6.7 g, 58.8%). Recrystallization from ethyl acetate-hexane afforded colorless plates. m.p. 162°-163° C. Elemental analysis for C21H18N2O4S, Calcd.: C, 63.95; H, 4.60; N, 7.10. Found: C, 63.84; H, 4.63; N, 6.90. This product showed the IR and NMR spectra in accordance with those of the compound obtained in Example 6.

Workup

  1. extractionThe aqueous mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe oily residue was chromatographed on a column of silica gel (200 g)
  6. washfrom the fractions eluted with chlorform-methanol (100:1, V/V)

Sources & evidence

ORD record
ord-8b6234674c5d40d897dae8a634dc35f0
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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