Reaktion #88332

Reaktionsgleichung

(S)-2-(4-nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide salt

CaCO3

thiophosgene

→

desired product

Ausbeute 93.0%

(S)-4-[1-isothiocyanato-2-(4-nitrophenyl)-ethyl]-2-phenylthiazole

Ausbeute 93.0%

Lösungsmittel

CH2Cl2

water

CCl4 water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers are separated
2. 2
   Extraktionthe aqueous layer extracted with CH2Cl2
3. 3
   WaschenThe combined organic layers are washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo to a residue that
6. 6
   Sonstigeis purified over silica (CH2Cl2)

Vorschrift

To a solution of (S)-2-(4-nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide salt, 52, (2.03 g, 5 mmol) and CaCO3 (1 g, 10 mmol) in CCl4/water (10:7.5 mL) is added thiophosgene (0.46 mL, 6 mmol). The reaction is stirred at room temperature for 18 hours then diluted with CH2Cl2 and water. The layers are separated and the aqueous layer extracted with CH2Cl2. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated in vacuo to a residue that is purified over silica (CH2Cl2) to afford 1.71 g (93% yield) of the desired product. ESI+ MS 368 (M+1).

Quelle