반응 #1442490

반응 방정식

KBr

Triethylene tetramine

methacryloyl chloride

→

Tetra methacryloyl triethylene tetramine

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was continued stirring at room temperature overnight
2. 2
   기타the suspension formed
3. 3
   여과was filtered
4. 4
   추출The filtrate was extracted with NaOH (aq)
5. 5
   기타The water was rotary evaporated
6. 6
   세척the residue was washed with acetone
7. 7
   여과filtered
8. 8
   농축The acetone filtrate was concentrated down
9. 9
   기타to obtain a white solid
10. 10
    기타The solid is recrystallized from diethyl ether
11. 11
    기타to give white crystals, m.p. 168-170° C

실험 절차

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.

출처