Water → 5-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzylidene]-2,4-thiazolidinedione

HRID 4393

Reaction equation

HRID 4393 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25].O>CN(C)C=O.C(O)(=O)C>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:21][C:20]=1[CH2:19][O:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5178225-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 542390285-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzylidene]-2,4-thiazolidinedioneYield 41.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.664 g) in N,N-dimethylformamide (20 ml), and the mixture was stirred for 30 minutes. A solution of 4-chloromethyl-5-methyl-2-phenyloxazole (0.623 g) in N,N-dimethylformamide (10 ml) was added dropwise to the mixture under ice-cooling. After stirring at room temperature for 5 hours, the reaction solution was poured into water. The aqueous mixture was made acid with acetic acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on a column of silica gel (50 g). From the fractions eluted with ethyl acetatehexane (1:2, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidene]-2,4-thiazolidinedione (0.49 g, 40.8%). Recrystallization from chloroform-methanol afforded colorless prisms, m.p. 225°-226° C. Elemental analysis for C21H16N2O4S, Calcd.: C, 64.27; H, 4.11; N, 7.14. Found: C, 64.49; H, 3.96; H, 6.86.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 5 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a column of silica gel (50 g)
  8. washFrom the fractions eluted with ethyl acetatehexane (1:2, V/V)

Sources & evidence

ORD record
ord-59eb3a84c5114e449b61d0353ae198d1
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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