反応 #1442489

反応方程式

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

溶媒

dichloromethane

dichloromethane

反応条件

後処理

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

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