Thiazolidinedione → 5-[3-(Phenylmethoxy)phenylmethyl-ene]-2,4-thiazolidinedione

HRID 1728320Notes

Reaction equation

HRID 1728320 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].N1CCCCC1>N1C=CC=CC=1>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:21]3[S:17][C:18](=[O:23])[NH:19][C:20]3=[O:22])[CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 743423-Benzyloxybenzaldehyde

Product 1

HCID 12494175-[3-(Phenylmethoxy)phenylmethyl-ene]-2,4-thiazolidinedioneYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-benzyloxybenzaldehyde (42.45 g, 200 mmol), 2,4-thiazolidinedione (23.43 g, 200.0 mmol), and piperidine (2 g) in 150 ml pyridine was refluxed for 16 h. The mixture was concentrated in vacuo, and the residue was triturated with 500 ml hot benzene, filtered, and the filtrate left standing at room temperature for two days. The resulting crystals were collected by filtration, washed with petroleum ether, and dried to give the product in 100% yield; mp 233-235° C.; IR (nujol): 1741, 1688 (CO) cm-1 ; NMR (DMSOd6TMS): δ5.19 (s, 2H, ArCH2), 7.15-7.25 (m, 3H), 7.3-7.5 (m, 6H), 7.73 (s, 1H, C=CH); Anal calcd for C17H13NO3, MW 311.36: C, 65.58; H, 4.21; N, 4.50; S, 10.30. Found: C, 65.53; H, 3.91; N, 4.52; S, 10.30. Mass spec m/e 312(M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated with 500 ml hot benzene
  3. filtrationfiltered
  4. waitthe filtrate left
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with petroleum ether
  7. customdried
  8. customto give the product in 100% yield

Sources & evidence

ORD record
ord-b07df93b035f47fb8f7171a8c9c1051f
Source dataset
uspto-grants-1994_07
Patent number
US05326770

Reaction notes

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