Reaction #1884951

Reaction equation

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

iodochloride

CH2Cl2

→

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

Yield 76.0%

Solvents

acetic acid

Conditions

Workup

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

Procedure

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).

Source