Reaktion #655148

Reaktionsgleichung

2-tert-butyldimethysilyloxy-4-nitroaniline

NaHCO3

thiophosgene

→

titled compound

Ausbeute 98.0%

N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N′-phenyl-thiourea

Ausbeute 98.0%

Lösungsmittel

CHCl3 H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeN-(2-tert-Butyldimethysilyloxy-4-nitrophenyl)-N′-phenyl-thiourea was prepared
2. 2
   SonstigeThe CHCl3 layer was separated
3. 3
   Trocknendried over sodium sulfate
4. 4
   EinengenThe solution was concentrated in vacuo
5. 5
   workup.DISSOLUTIONthe residue was dissolved in toluene
6. 6
   workup.ADDITIONtreated with aniline (100 uL) at 23° C. for 12 h
7. 7
   EinengenThe reaction mixture was concentrated
8. 8
   Sonstigethe residue was purified by flash chromatography (10% EtOAc/hexanes)

Vorschrift

N-(2-tert-Butyldimethysilyloxy-4-nitrophenyl)-N′-phenyl-thiourea was prepared by treating a biphasic solution of 2-tert-butyldimethysilyloxy-4-nitroaniline(80 mg, 0.308 mmol) and NaHCO3 in CHCl3:H2O(2.5:1, 7 mL) with thiophosgene at 0° C. The solution was allowed to warm to 23° C. and the reaction was continued overnight The CHCl3 layer was separated and dried over sodium sulfate. The solution was concentrated in vacuo and the residue was dissolved in toluene and treated with aniline (100 uL) at 23° C. for 12 h. The reaction mixture was concentrated and the residue was purified by flash chromatography (10% EtOAc/hexanes) to afford the titled compound as a yellow solid (120.8 mg, 98%) mp: 144-145° C.; 1H NMR (CD3OD/CDCl3): δ 8.65 (d, 1H, J=10.0 Hz), 7.58 (d, 1H, J=10.0 Hz), 7.47 (d, 1H, J=1.25 Hz), 7.26 (m, 4H), 7.10 (m, 1H).

Quelle