Reaktion #512077

Reaktionsgleichung

ammonia

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

CaCO3

thiophosgene

→

desired product

(S)-1-[1-(thiophen-2-ylthiazol-4-yl)-2-(4-nitrophenyl)ethyl]-thiourea

Lösungsmittel

CCl4 water

CH2Cl2

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 which
6. 6
   Sonstigeis purified over silica

Vorschrift

To a solution of (S)-2-(4-nitrophenyl)-1-(thiophen-2-ylthiazol-4-yl)ethanamine hydrobromide salt, 8, (1.23 g, 2.98 mmol) and CaCO3 (0.597 g, 5.96 mmol) in CCl4/water (10 mL/5 mL) is added thiophosgene (0.412 g, 3.58 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 which is subsequently treated with ammonia (0.5M in 1,4-dioxane, 29.4 mL, 14.7 mmol) which is purified over silica to afford 0.490 g of the desired product as a red-brown solid. ESI+ MS 399 (M+1).

Quelle