Реакция #1442490

Уравнение реакции

KBr

Triethylene tetramine

methacryloyl chloride

→

Tetra methacryloyl triethylene tetramine

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction was continued stirring at room temperature overnight
2. 2
   Другоеthe suspension formed
3. 3
   Фильтрацияwas filtered
4. 4
   ЭкстракцияThe filtrate was extracted with NaOH (aq)
5. 5
   ДругоеThe water was rotary evaporated
6. 6
   Промывкаthe residue was washed with acetone
7. 7
   Фильтрацияfiltered
8. 8
   КонцентрированиеThe acetone filtrate was concentrated down
9. 9
   Другоеto obtain a white solid
10. 10
    ДругоеThe solid is recrystallized from diethyl ether
11. 11
    Другоеto give white crystals, m.p. 168-170° C

Методика

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.

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