Hydrochloric Acid → HCID 10993238, compound

HRID 1739017Notes

Reaction equation

HRID 1739017 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:6][CH:5]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26].Cl>CN(C)C=O.O>[CH3:26][C:25]1[O:24][C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:22][C:21]=1[CH2:20][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 11806663HCID 11806663, compound

Product 1

HCID 10993238HCID 10993238, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Oily sodium hydride (60%, 0.10 g) was added to a solution of 5-[2-(4-hydroxyphenyl)ethyl]-2,4-thiazolidinedione (0.30 g) in N,N-dimethylformamide (20 ml), and the mixture was stirred at room temperature for 15 minutes. Then, 4-chloromethyl-5-methyl-2-phenyloxazole (0.29 g) was added, and the mixture was stirred at 90 to 100° C. for 2 hours. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-chloroform (1:9, v/v) gave 5-[2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl]-2,4-thiazolidinedione (0.30 g, 59%). This product was recrystallized from dichloromethane-isopropyl ether. Colorless needles. mp: 146-147° C.

Workup

  1. stirringthe mixture was stirred at 90 to 100° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with ethyl acetate-chloroform (1:9, v/v)

Sources & evidence

ORD record
ord-f864598aa67f4c1e9a08d5b60a2a2ed3
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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