Reaktion #1119118

Reaktionsgleichung

4-methyl-5-thiazole carboxylic acid

thionyl chloride

ethyl acetate

4-amino-1,1,3-trimethylindane

→

amorphous solid

Ausbeute 51.7%

4-methyl-N-(1,1,3-trimethylindan-4-yl)thiazole-5-carboxamide

Ausbeute 51.7%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 hour
2. 2
   workup.DISTILLATIONThe reaction solution was distilled under reduced pressure
3. 3
   Sonstigeto remove excess thionyl chloride
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 10 ml of ethyl acetate
5. 5
   WaschenThe solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine
6. 6
   TrocknenThe solution was dried with magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe concentrated residue was separated
9. 9
   Sonstigepurified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2)

Vorschrift

A mixture of 1.7 g (10.3 mmols) of 4-methyl-5-thiazole carboxylic acid and 10 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The residue was dissolved in 10 ml of ethyl acetate. The solution was added to 10 ml of an ethyl acetate solution of 1.8 g (10.3 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine. The solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2), to obtain 1.6 g of amorphous solid substance (Compound No. 6 shown in Table 4). The yield was 50.2%.

Quelle