Benzaldehyde → HCID 54339345, compound

HRID 1588760Notes

Reaction equation

HRID 1588760 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[OH-].[Na+].CO>[C:19]1([CH:18]=[CH:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH:10]=[C:11]3[S:15][C:14](=[O:16])[NH:13][C:12]3=[O:17])=[CH:8][CH:9]=2)=[O:3])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 54398857HCID 54398857, compound

Product 1

HCID 54339345HCID 54339345, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-(4-acetylphenylmethylene)thiazolidine-2,4-dione (1.0 g, 4.0 mmol) and benzaldehyde (0.62 ml, 6.1 mmol) in 1N NaOH (14 ml) and methanol (25 ml) was stirred for 1 hour at 0° C. and then at room temperature for 3 days, the precipitate was collected and dissolved in water, and this solution was acidified with 2N HCl and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (30 ml), dried over sodium sulfate and concentrated in vacuo, leaving the free acid form of title product (0.4 g, 29%) as a yellow solid. The latter was converted to sodium salt according to the method of Example 42.

Workup

  1. customthe precipitate was collected
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined extracts were washed with brine (30 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2f547530fb24d1f84d2ca1b21204224
Source dataset
uspto-grants-1993_06
Patent number
US05223522

Reaction notes

Loading…