Reaction #5386

Reaction equation

HCl

2-aminoethyl methacrylate hydrochloride

3,4,5-Triacetoxybenzoyl chloride

triethylamine

→

2-(3,4,5-triacetoxybenzamido)ethyl methacrylate

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe organic layer was isolated
2. 2
   Washwashed with saturated NaHCO3 and 50 mL 1N HCl
3. 3
   Dryingdried over MgSO4
4. 4
   Otherevaporated
5. 5
   Otherto give an oil, which
6. 6
   Othercrystallized rapidly
7. 7
   workup.ADDITIONafter the addition of 50 mL diethyl ether
8. 8
   OtherThe product was isolated by filtration and vacuum
9. 9
   Otherdried
10. 10
    OtherYield

Procedure

3,4,5-Triacetoxybenzoyl chloride (0.050 mol) was dissolved in 100 mL CH2Cl2 at 0° C. To this was added 2-aminoethyl methacrylate hydrochloride (8.28 g, 0.050 mol), followed by dropwise addition of triethylamine (14.63 mL, 0.105 mol). After 30 min, 100 mL 1N HCl was added with vigorous stirring. The organic layer was isolated, washed with saturated NaHCO3 and 50 mL 1N HCl, dried over MgSO4, and evaporated to give an oil, which crystallized rapidly after the addition of 50 mL diethyl ether. The product was isolated by filtration and vacuum dried. Yield, 17.97 g as a white solid, 88%. 1H NMR (300 MHz, CDCl3), δ1.92 (s, 3H), 2.26 (s, 6H), 2.27 (s, 3H), 3.68 (m, 2H), 4.30 (t, 2H), 5.58 (m, 1H), 6.11 (s, 1H), 6.66 (t, broad, 1H), 7.51 (s, 2H). Anal., calcd for C19H21N1O9C 56.02, H 5.20, N 3.44, found C 55.99, H 5.15, N 3.50.

Source