反应 #336805

反应方程式

fluorescein isothiocyanate

Et3N

→

fluorescein

溶剂

DMF

CH2Cl2

反应条件

后处理

1. 1
   其他An orange colored precipitate was immediately formed
2. 2
   其他remained during the entire period of the reaction
3. 3
   其他After completion of the reaction
4. 4
   过滤the insoluble precipitate was filtered off
5. 5
   其他and the solvent was removed under reduced pressure
6. 6
   workup.ADDITIONThe residue was diluted with CH2Cl2 (15 mL)
7. 7
   洗涤washed with 1N HCl (2×15 mL) and H2O (2×15 mL)
8. 8
   干燥The organic phase was dried over anhydrous Na2SO4
9. 9
   其他evaporated under reduced pressure

实验过程

The starting amine (5) (0.15 g, 0.12 mmol) and fluorescein isothiocyanate (FLITC) (0.056 g, 0.14 mmol) were dissolved in a mixture of DMF and CH2Cl2 (6 mL, 1:5 ratio) at room temperature. The reaction was cooled to 0° C., and then an excess amount of Et3N (66 μL, 0.48 mmol) was added dropwise. An orange colored precipitate was immediately formed and remained during the entire period of the reaction. After completion of the reaction, the insoluble precipitate was filtered off; and the solvent was removed under reduced pressure. The residue was diluted with CH2Cl2 (15 mL), washed with 1N HCl (2×15 mL) and H2O (2×15 mL). The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure to afford 0.18 g (92%) of fluorescein-labeled guanidine (17) as an orange colored foam-shaped solid. 1H NMR (CD3OD): δ 8.20 (s, 1H, ArH), 7.86 (m, 1H, ArH), 7.22 (m, 2H, ArH), 6.64 (m, 3H, ArH), 6.56 (m, 2H, ArH), 3.86 (m, 2H, CH2NHCS), 3.66 (m, 12H, CH2O), 3.46 (m, 6H, CH2NHCO), 3.38 (m, 6H, CH2NH), 2.58 (m, 2H, CH2CO), 2.42 (m, 6H, CH2CO), 1.48 (s, 27H, t-Bu), 1.46 (s, 27H, t-Bu).

来源