Reaktion #1442490

Reaktionsgleichung

KBr

Triethylene tetramine

methacryloyl chloride

→

Tetra methacryloyl triethylene tetramine

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was continued stirring at room temperature overnight
2. 2
   Sonstigethe suspension formed
3. 3
   Filtrationwas filtered
4. 4
   ExtraktionThe filtrate was extracted with NaOH (aq)
5. 5
   SonstigeThe water was rotary evaporated
6. 6
   Waschenthe residue was washed with acetone
7. 7
   Filtrationfiltered
8. 8
   EinengenThe acetone filtrate was concentrated down
9. 9
   Sonstigeto obtain a white solid
10. 10
    SonstigeThe solid is recrystallized from diethyl ether
11. 11
    Sonstigeto give white crystals, m.p. 168-170° C

Vorschrift

Triethylene tetramine (2.93 g, 0.02 moles) in dichloromethane (100 ml) was added drop wise over 6 hrs to a solution of methacryloyl chloride (8.32 g, 0.08 moles) in dichloromethane (40 ml), stirring vigorously at room temperature. The reaction was continued stirring at room temperature overnight and the suspension formed was filtered. The filtrate was extracted with NaOH (aq). The water was rotary evaporated and the residue was washed with acetone and filtered. The acetone filtrate was concentrated down and put through a silica gravity chromatography column with acetone as the elutant to obtain a white solid. The solid is recrystallized from diethyl ether to give white crystals, m.p. 168-170° C. 1H n.m.r. (D2O) δ, 5.71(19.7 Hz), 5.51 (7.8 Hz), 5.31(9.7 Hz), 5.06 (17.7 Hz), (8 H, d×4) C—CH2; 3.61 (6 H, m) N—CH2—CH2; 3.48(6 H, m) N—CH2—CH2; 1.96(4.1 Hz); 1.93(5.8 Hz); 1.91(6.0 Hz); 1.88(4.5 Hz), (12 H, d×4) CH3; 13C n.m.r. (D2O), δ 178.76, 178.70, 174.71, 174.61 (C=O); 142.19, 142.0, 141.71, 141.56 (C=CH2), 124.52, 124.19, 120.06, 119.60 (C=CH2); 22.30, 22.20, 20.48; (CH3), 50.33, 49.22, 46.45, 44.00, 40.22, 39.49 (N—CH2—CH2). MS: mz: 419.3 (MH+, 100%), 391.3(4), 266.2(10), 223.1(42); HRMS: found: 419.26695 C22H34N4O4 requires 418.5299. Elemental analysis: found: C, 62.97; H, 8.09; N, 13.31; C22H34N4O4 requires C, 63.13; H, 8.19; N, 13.39. I.R. (KBr) (CM−1) 3353, 1665, 1650, 1530, 1279.

Quelle