Benzoic Acid → 5-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dione

HRID 2211465Notes

Reaction equation

HRID 2211465 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:20][CH2:21][CH3:22])[N:5]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)[C:6](=[O:8])[CH:7]=1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[N:3]=[C:4]([CH2:20][CH2:21][CH3:22])[N:5]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:14][CH:13]=2)[C:6](=[O:8])[CH:7]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 118227094-[2-[4-Methyl-2-propyl-6-oxo 1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde

Product 1

HCID 539648275-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dioneYield 125.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde (10 g, 24.5 mmol) (obtained from preparation 1), thiazolidine-2,4-dione (3.5 g, 30 mmol), benzoic acid (388 mg, 3.18 mmol) and piperidine (352 μl, 303 mg, 3.68 mmol) in toluene (50 ml) was refluxed for 1 h with continuous removal of water. The reaction was cooled to room temperature and the resultant crystalline compound was filtered and washed with water and dried to afford the title compound (12.3 g, 99%), mp 240-242° C.

Workup

  1. filtrationthe resultant crystalline compound was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d031a43d6fc24256b868b2415fd79acb
Source dataset
uspto-grants-2006_09
Patent number
USRE039266E1

Reaction notes

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