반응 #1442489

반응 방정식

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature overnight
2. 2
   여과the suspension was filtered
3. 3
   추출The filtrate was extracted with NaOH(aq)
4. 4
   기타The water was rotary evaporated
5. 5
   세척the residue was washed with acetone
6. 6
   여과filtered
7. 7
   농축The acetone washings were concentrated down
8. 8
   기타A yellow solid was obtained
9. 9
   기타recrystallized with cold diethyl ether
10. 10
    기타to give white crystals, m.p. 107-109.5° 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 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.

출처