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

HRID 1368099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368099
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 539648275-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dioneAusbeute 125,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f4d381f49af049a89bcc7ae7621557ef
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573268B1

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