Acetic Acid → 5-[4-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)ethoxy]benzylidene]-2,4-thiazolidinedione

HRID 726563Notes

Reaction equation

HRID 726563 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][N:3]1[CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][N:3]1[CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:27]2[S:23][C:24](=[O:29])[NH:25][C:26]2=[O:28])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 109025664-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-ethoxy]benzaldehyde2×

Product 1

HCID 571682695-[4-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)ethoxy]benzylidene]-2,4-thiazolidinedioneYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 g (17 mM) of 4-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)ethoxy]benzaldehyde (Compound 4A) and 2.1 (18 mM) of 2,4-thiazolidinedione were dissolved in 150 ml of toluene. After the addition of a catalytic amount of acetic acid and piperidine, the mixture was reacted for two hours with heating while refluxing in a Dean Stark apparatus. After confirming completion of the reaction by TLC, the reaction mixture was gradually returned to room temperature. The resulting crystals were collected by filtration and washed with a small amount of toluene and then with hexane, and dried under vacuum at 50° C, to obtain 5.8 g (yield 87%) of the title compound as pale yellow crystals.

Workup

  1. customthe mixture was reacted for two hours
  2. temperaturewith heating
  3. temperaturewhile refluxing in a Dean Stark apparatus
  4. customcompletion of the reaction by TLC
  5. customwas gradually returned to room temperature
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with a small amount of toluene
  8. dry with materialwith hexane, and dried under vacuum at 50° C

Sources & evidence

ORD record
ord-ddefe8a156434b09a46a20de3b1e616a
Source dataset
uspto-grants-1998_01
Patent number
US05710152

Reaction notes

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