반응 #1884951

반응 방정식

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

iodochloride

CH2Cl2

→

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

수율 76.0%

용매

acetic acid

반응 조건

후처리

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

실험 절차

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).

출처