Reaction #985289

Reaction equation

2-(pyridin-2-yldisulfanyl) -ethyl-ammonium chloride

EDC

ferrocenecarboxylic acid

N-hydroxysuccinimide

Et3N

→

12

Ferrocene-2-carboxylic acid [2-(pyridin-2-yldisulfanyl)-ethyl]-amide

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   workup.DISSOLUTIONThe crude residue was dissolved in 8 mL of DMF
3. 3
   workup.STIRRINGAfter stirring for 48 h
4. 4
   Otherthe solvent was evaporated in vacuo
5. 5
   OtherThe crude residue was purified by flash chromatography (gradient: hexanes/EtOAc, 1:1, v/v to EtOAc)

Procedure

EDC (213 mg, 1.1 mmol) was added to a solution of ferrocenecarboxylic acid (232 mg, 1.0 mmol) and N-hydroxysuccinimide (128 mg, 1.1 mmol) dissolved in 20 mL of CH2Cl2. The solution was stirred at room temperature for 5 h and concentrated. The crude residue was dissolved in 8 mL of DMF and 2-(pyridin-2-yldisulfanyl) -ethyl-ammonium chloride (222 mg, 1.0 mmol) was added followed by Et3N (0.14 mL, 1.0 mmol). After stirring for 48 h, the solvent was evaporated in vacuo. The crude residue was purified by flash chromatography (gradient: hexanes/EtOAc, 1:1, v/v to EtOAc) to afford 113 mg (28% over 2 steps) of 12. 1H NMR 400 MHz (CDCl3) d 8.56 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 7.43 (t, J=6.8 Hz, 1H), 7.15 (m, 1H), 4.75 (m, 2H), 4.34 (m, 2H), 4.20 (s, 5H), 3.63 (q, J=6.0 Hz, 2H), 2.98 (t, J=6.0 Hz, 2H).

Source