反応 #1442490

反応方程式

KBr

Triethylene tetramine

methacryloyl chloride

→

Tetra methacryloyl triethylene tetramine

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was continued stirring at room temperature overnight
2. 2
   その他the suspension formed
3. 3
   ろ過was filtered
4. 4
   抽出The filtrate was extracted with NaOH (aq)
5. 5
   その他The water was rotary evaporated
6. 6
   洗浄the residue was washed with acetone
7. 7
   ろ過filtered
8. 8
   濃縮The acetone filtrate was concentrated down
9. 9
   その他to obtain a white solid
10. 10
    その他The solid is recrystallized from diethyl ether
11. 11
    その他to give white crystals, m.p. 168-170° C

実験手順

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.

出典