Reaktion #1752630

Reaktionsgleichung

8d

N-formyl-2,6-diethylaniline

phosphorus pentasulfide

Na2CO3

4-Chloro-2-butanone

→

9d

Ausbeute 98.4%

3-(2,6-diethylphenyl)-4,5-dimethylthiazolium chloride

Ausbeute 98.4%

Lösungsmittel

1,4-dioxane

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting slurry was heated at 100° C
2. 2
   TemperaturThe reaction mixture was refluxed for 50 min
3. 3
   TemperaturAfter cooling at room temperature
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigepurified by column chromatography (column packed with silica gel)
6. 6
   Wascheneluting with EtOH/CH2Cl2 (15/85)
7. 7
   SonstigeUpon concentration of the last band, a viscous brownish oil was obtained
8. 8
   Waschenwashed
9. 9
   workup.STIRRINGunder vigorous stirring with diethyl ether (3×2 mL)

Vorschrift

A mixture of 8d (3.545 g, 20 mmol) and phosphorus pentasulfide (0.900 g, 2.02 mmol) in dry 1,4-dioxane (5 mL) was stirred at room temperature for 15 min under an argon atmosphere. 4-Chloro-2-butanone (1.422 g, 20 mmol) was added and the resulting slurry was heated at 100° C. The reaction mixture was refluxed for 50 min, initially becoming clear yellow and finally deep red. After cooling at room temperature, the crude mixture was diluted with H2O (20 mL). Na2CO3 was added to the reaction mixture until pH≈7. The solvent was evaporated under reduced pressure and the resulting solid was suspended in CH2Cl2 and purified by column chromatography (column packed with silica gel) eluting with EtOH/CH2Cl2 (15/85). Upon concentration of the last band, a viscous brownish oil was obtained. This was solidified when washed under vigorous stirring with diethyl ether (3×2 mL) to afford 9d as a tan solid (560 mg, 10%). 1H NMR (CDCl3. 300 MHz): δ=10.97 (s, 1H), 7.52 (t, J=8 Hz, 1H), 7.30 (d, J=8 Hz, 2H), 2.63 (s, 3H), 2.16 (q, J=8 Hz, 4H), 2.06 (s, 3H), 1.14 (t, J=8 Hz, 6H); 13C{1H} NMR (CDCl3, 75 MHz): δ=161.92, 141.63, 139.62, 135.04, 134.20, 132.30, 127.65, 23.97, 14.18, 13.16, 11.82; HRMS (FAB+) calculated for C15H20NS [M]+ 246.1316, observed 246.1326.

Quelle