2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Ethyl-N'-[7-(phenylsulfanyl)-1,3-benzothiazol-2-yl]urea
반응식
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]참가 물질
4
반응 조건
- 온도
- 20 °C
실험 절차
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.