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

HRID 1602889Notes

Reaction equation

HRID 1602889 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 mixture 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-80d867c7adc84e57973e79cd8ab9ed2b
Source dataset
uspto-grants-1999_11
Patent number
US05985884

Reaction notes

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