反応 #11197

反応方程式

Water

bromide

6-(3-Bromopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

thiophenol

triethylamine

→

4-(2-Chlorophenyl)-9-hydroxy-6-[3-(phenylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

溶媒

p-dioxane

反応条件

後処理

1. 1
   温度was refluxed for 16 h
2. 2
   抽出the mixture was extracted with ethyl acetate
3. 3
   その他The organic layer was dried
4. 4
   その他the drying agent was removed
5. 5
   濃縮the solution was concentrated to dryness the sulfide (131) directly (37.2 mg, 85%), which
6. 6
   その他crystallised from ethyl acetate/petroleum ether as an orange powder, mp 229–231° C

実験手順

A solution of the bromide (58) (41 mg, 0.085 mmol) prepared as described in example 172, thiophenol (9.5 μL, 0.093 mmol) and triethylamine (0.25 mL, 3.40 mmol) in p-dioxane (1.5 mL) was refluxed for 16 h. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness the sulfide (131) directly (37.2 mg, 85%), which crystallised from ethyl acetate/petroleum ether as an orange powder, mp 229–231° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.37 (s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.76 (s, 1H), 7.60–7.42 (m, 5H), 7.25–7.19 (m, 4H), 7.16–7.10 m, 2H), 4.57 (t, J=6.8 Hz, 2H), 2.98 (m, 2H), 2.01 (m, 2H). Found: C, 67.36; H, 4.29; N, 5.36. C29H21ClN2SO3.114H2O requires C, 67.31; H, 4.19; N, 5.41.

出典