Methanethioamide → 3-(5-Methyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265620
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH3:12])[CH:5]=1.[CH:16]([NH2:18])=[S:17]>CCO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:18]=[CH:16][S:17][C:11]=2[CH3:12])[CH:5]=1

Komponenten

4

Edukt 2

HCID 3005587MethanethioamideHCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Produkt 1

HCID 696892723-(5-Methyl-thiazol-4-yl)-benzoic acid methyl esterAusbeute 103,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of crude rac-3-(2-bromo-propionyl)-benzoic acid methyl ester (2.71 g) and thioformamide (1.83 g) in EtOH (20 ml) was heated at reflux for 1 h. The mixture was partitioned between AcOEt and brine, the organic layer was dried and evaporated and the residual oil was chromatographed on silica gel using AcOEt/hexane (1:4) as eluent to give 3-(5-methyl-thiazol-4-yl)-benzoic acid methyl ester (2.41 g) as white solid.

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. customThe mixture was partitioned between AcOEt and brine
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residual oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8956c7edb5fb4156b7f7c6f7c2d66b5f
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544985B2

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