Reaktion #1772007

Reaktionsgleichung

2-(4′-aminophenyl)-6-methoxy benzothiazole

iodochloride

CH2Cl2

→

2-(4′-amino-3′-iodophenyl)-6-methoxy benzothiazole

Ausbeute 76.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe glacial acetic acid was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   Sonstigethe aqueous layer was separated
4. 4
   Extraktionextracted with CH2Cl2
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigethe evaporation of the solvent
7. 7
   Sonstigethe residue was purified by preparative TLC(Hexanes:ethyl acetate=6:1)

Vorschrift

To a solution of 2-(4′-aminophenyl)-6-methoxy benzothiazole (22 mg, 0.09 mmol) in glacial acetic acid (2.0 mL) was injected 1 M iodochloride solution in CH2Cl2 (0.10 mL, 0.10 mmol, 1.2 eq.) under N2 atmosphere. The reaction mixture was stirred at room temperature for 16 hr. The glacial acetic acid was removed under reduced pressure and the residue was dissolved in CH2Cl2. After neutralizing the solution with NaHCO3, the aqueous layer was separated and extracted with CH2Cl2. The organic layers were combined and dried over MgSO4. Following the evaporation of the solvent, the residue was purified by preparative TLC(Hexanes:ethyl acetate=6:1) to give 2-(4′-amino-3′-iodophenyl)-6-methoxy benzothiazole (25 mg, 76%) as brown solid. 1HNMR (300 MHz, CDCl3) δ (ppm): 8.35 (d, J=2.0 Hz, 1H), 7.87 (dd, J1=2.0 Hz, J2=9.0 Hz, 1H), 7.31 (d, J=2.2 Hz, 1H), 7.04 (dd, J1=2.2 Hz, J2=9.0 Hz, 1H), 6.76 (d, J=9.0 Hz, 1H), 3.87 (s, 3H).

Quelle