2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Ethyl-N'-[7-(phenylsulfanyl)-1,3-benzothiazol-2-yl]urea

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-ethyl-N′-[7-(phenylsulfanyl)-4,5-dihydro-1,3-benzothiazol-2-yl]urea (crude product from the previous reaction, 1.59 mmol) in toluene (35.0 mL) was added DDQ (500 mg, 2.17 mmol). The reaction mixture was stirred at about 20° C. for about 2 hrs. The toluene was removed in vacuo and the crude material was taken up in CH2Cl2. The organic phase was washed with 0.5 M NaOH (2 times) and dried over MgSO4. The crude oil was purified by flash chromatography on SiO2 (EtOAc/CH2Cl2 5/95). 445 mg (85%, 2 steps) of pure product was isolated. LC/MS 330 (MH+); RP-HPLC RT 17.56 min.

Provenance & Evidence