N-(4-(2,2-Dicyanoethenyl)phenyl)acetamide → N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide

HRID 1172228

Reaktionsgleichung

Reaktionsgleichung von HRID 1172228
[Na].[NH2:2][C:3]([NH2:5])=[S:4].[C:6]([C:8]([C:20]#[N:21])=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)#[N:7]>C(O)C>[NH2:21][C:20]1[C:8]([C:6]#[N:7])=[C:9]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[NH:2][CH:3]([SH:4])[N:5]=1

Komponenten

5

Edukt 3

HCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamideHCID 2723790ThioureaHCID 5360545Sodium

Produkt 1

HCID 86621820N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamideAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 20 mL of absolute ethanol, 250 mg of metallic sodium was added in small portions. After dissolved completely, 760 mg of thiourea was added to the above solution, and the mixture was stirred at room temperature for 1 hour. To the reaction, 2.11 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide was added, and the mixture was heated to reflux for 3 hours. Then, the solvent was removed under reduced pressure from the reaction mixture, the residue was dissolved in 30 mL of water. In addition, the mixture was acidified by adding acetic acid in small portions, thereto 30 mL of ethyl acetate was added and then the solution was stirred overnight. Filtration of the precipitated material gave 1.2 g of N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide as a white powder.

Aufarbeitung

  1. dissolutionAfter dissolved completely
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 hours
  5. customThen, the solvent was removed under reduced pressure from the reaction mixture
  6. dissolutionthe residue was dissolved in 30 mL of water
  7. additionby adding acetic acid in small portions
  8. addition30 mL of ethyl acetate was added
  9. stirringthe solution was stirred overnight
  10. filtrationFiltration of the precipitated material

Quellen und Nachweise

ORD-Eintrag
ord-0d7f92e212674c2f9cf27192a2404cf8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834002B2

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