反应 #1442489

反应方程式

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature overnight
2. 2
   过滤the suspension was filtered
3. 3
   萃取The filtrate was extracted with NaOH(aq)
4. 4
   其他The water was rotary evaporated
5. 5
   洗涤the residue was washed with acetone
6. 6
   过滤filtered
7. 7
   浓缩The acetone washings were concentrated down
8. 8
   其他A yellow solid was obtained
9. 9
   其他recrystallized with cold diethyl ether
10. 10
    其他to give white crystals, m.p. 107-109.5° C

实验过程

Triethylene tetramine (2.93 g, 0.02 moles) in dichloromethane (100 ml) was added drop wise over 6 hrs to a solution of acryloyl chloride (7.24 g, 0.08 moles) in dichloromethane (40 ml), stirring vigorously at room temperature. The reaction was stirred at room temperature overnight and the suspension 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 washings were concentrated down and the yellow oil remaining was put through a silica gravity chromatography column with acetone as the elutant. A yellow solid was obtained and recrystallized with cold diethyl ether to give white crystals, m.p. 107-109.5° C. 1H n.m.r (D2)) δ6.60(4 H, m) CH═CH2;6.16 (6 H, m), CH═CH2; 5.79(2 H, m), CH═CH2;3.61 (6 H, m) N—CH2—CH2,3.52(6 H, m) N—CH2—CH2. 13C n.m.r (D2)) δ172.52, 172.39, 171.78, 171.70 (C═O); 132.70, 132.55, 132.14, 131.74 (CH═CH2), 130.52, 130.32, 129.93, 129.64 (CH═CH2), 50.35, 49.82, 49.35, 48.31, 47.33, 46.05 (NH—CH2—CH2). MS: mz: 363.2 (MH+, 100%), 291.2 (16), 238.1(6), 195.1(74); HRMS: found:363.20204; C18H26N4O4 requires: 362,4236Elemental analysis: found: C, 59.71; H, 7.22; N, 15.37; C18H26N4O4 requires C, 59.65; H, 7.23; N, 15.46. L.R. (KBr) (cm−1): 3283, 3423, 1672, 1642, 1552, 1278.

来源