HCID 3145500, Verbindung → HCID 15392100, Verbindung

HRID 619125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619125
Br[CH:2]([C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12])[CH:3]=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([CH3:32])[NH:24][C:23](=[S:33])[NH:22]1>O1CCCC1>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:5]=1[C:2]1[S:33][C:23]2=[N:24][C:25]([CH3:32])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH3:13])[N:22]2[CH:3]=1

Komponenten

4

Edukt 2

HCID 3145500HCID 3145500, VerbindungHCID 11032855HCID 11032855, Verbindung

Produkt 1

HCID 15392100HCID 15392100, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2.0 g (7.5 mmol) of α-bromo-2,6-dichlorophenyl-acetaldehyde and 2.08 g (6.8 mmol) of ethyl (RS)-4-(2-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate in 40 ml of tetrahydrofuran was stirred at RT for 17 h. Subsequently, the mixture was cooled to 0° C. and the precipitated solid was filtered off, dissolved in 75 ml of conc. acetic acid and heated at reflux while stirring for 24 h. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate). There were obtained 1.82 g (51%) of ethyl (RS)-2-(2,6-dichlorophenyl)-5-(2-methoxyphenyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate as a yellow foam.

Aufarbeitung

  1. temperatureSubsequently, the mixture was cooled to 0° C.
  2. filtrationthe precipitated solid was filtered off
  3. dissolutiondissolved in 75 ml of conc. acetic acid
  4. temperatureheated
  5. temperatureat reflux
  6. stirringwhile stirring for 24 h
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue was purified by column chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9fc451155f804578a059127690f556e1
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958931

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