反応 #1772007

反応方程式

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

iodochloride

CH2Cl2

→

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

収率 76.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   その他The glacial acetic acid was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   その他the aqueous layer was separated
4. 4
   抽出extracted with CH2Cl2
5. 5
   乾燥dried over MgSO4
6. 6
   その他the evaporation of the solvent
7. 7
   その他the residue was purified by preparative TLC(Hexanes:ethyl acetate=6:1)

実験手順

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).

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