Reaktion #640580

Reaktionsgleichung

water

triethylamine

thiophosgene

2,2-Dimethyl-3-(2-nitrobenzylamino)-1-propanol

→

5,5-dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione

Ausbeute 88.8%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for one hour
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with a saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Vorschrift

2,2-Dimethyl-3-(2-nitrobenzylamino)-1-propanol (1.07 g, 4.50 mmol) was dissolved in chloroform (20 ml) and the reaction solution was cooled to 0° C. Then triethylamine (1.82 g, 18.0 mmol), thiophosgene (0.52 g, 4.50 mmol) was added thereto and stirred at a temperature as is for two hours and at room temperature for one hour. The reaction mixture was added with water, stirred at room temperature for one hour and then extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 5,5-dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione (1.12 g).

Quelle