반응 #336805

반응 방정식

fluorescein isothiocyanate

Et3N

→

fluorescein

용매

DMF

CH2Cl2

반응 조건

후처리

1. 1
   기타An orange colored precipitate was immediately formed
2. 2
   기타remained during the entire period of the reaction
3. 3
   기타After completion of the reaction
4. 4
   여과the insoluble precipitate was filtered off
5. 5
   기타and the solvent was removed under reduced pressure
6. 6
   workup.ADDITIONThe residue was diluted with CH2Cl2 (15 mL)
7. 7
   세척washed with 1N HCl (2×15 mL) and H2O (2×15 mL)
8. 8
   건조The organic phase was dried over anhydrous Na2SO4
9. 9
   기타evaporated under reduced pressure

실험 절차

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).

출처