2-(4-Chlorophenylsulfanyl)isoindole-1,3-(2H)-dione synthesis
- Product Name:2-(4-Chlorophenylsulfanyl)isoindole-1,3-(2H)-dione
- CAS Number:14204-31-0
- Molecular formula:C14H8ClNO2S
- Molecular Weight:289.74
Yield:14204-31-0 967 mg
Reaction Conditions:
with triethylamine in N,N-dimethyl-formamide;pentane; for 0.5 h;
Steps:
5.1.23 N-(4-chlorophenylthio)-phthalimide (28)
To a stirred solution of 4-chlorobenzenethiol (6.9mmol) in n-pentane (15mL), chlorine gas was added at 0°C until the solution turned red orange to obtain the sulfenyl chloride. The sulfenyl chloride solution was added dropwise to a stirred solution of phthalimide (6.9mmol) and TEA (9.0mmol) in DMF (15mL). The mixture was stirred for 30min, transferred to a large beaker, and then cold water was added. The suspension was filtered to give compound 28 as a solid (967mg, 48.4% yield). 1H NMR (400MHz, CDCl3): δ 7.93 (dd, J=8.6, 2.4Hz, 2H), 7.79 (dd, J=8.6, 2.4Hz, 2H), 7.57 (d, J=8.5Hz, 2H) and 7.29 (d, J=8.5Hz, 2H) ppm; mp: 179-182°C.
References:
Wu, Puhua;Zhang, Jiong;Meng, Qingqing;Nare, Bakela;Jacobs, Robert T.;Zhou, Huchen [European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75]
