Thiobenzamide → methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

HRID 2300590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300590
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH3:19])[C:12](=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15].CCOC(C)=O.O>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[CH3:19]

Komponenten

5

Edukt 3

HCID 683563ThiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22728543Water ethylacetate

Produkt 1

HCID 2775646methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 13.13 g (95.7 mmol) of thiobenzamide and 5.0 g (23.9 mmol) of methyl 4-bromo-3-oxo-pentanoate in 25 mL of dry toluene was heated at 90° C. for 5 h. The solution was poured into EtOAc/water and the aqueous phase extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered, and concentrated. The crude oil was purified by silica gel chromatography eluting with hexanes/EtOAc (3/1 to 2/1) to afford 4.14 g (70%) yield) of the title compound as a pale orange-colored oil: 1H NMR (CDCl3, 400 MHz) δ7.97 (m, 2H), 7.11 (m, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.36 (s, 3H).

Aufarbeitung

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by silica gel chromatography
  7. washeluting with hexanes/EtOAc (3/1 to 2/1)
  8. customto afford 4.14 g (70%)

Quellen und Nachweise

ORD-Eintrag
ord-cf0ac6c23b46432bb0488c8f91d5af47
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498174B1

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