Reaction #1442489

Reaction equation

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature overnight
2. 2
   Filtrationthe suspension was filtered
3. 3
   ExtractionThe filtrate was extracted with NaOH(aq)
4. 4
   OtherThe water was rotary evaporated
5. 5
   Washthe residue was washed with acetone
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe acetone washings were concentrated down
8. 8
   OtherA yellow solid was obtained
9. 9
   Otherrecrystallized with cold diethyl ether
10. 10
    Otherto give white crystals, m.p. 107-109.5° C

Procedure

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.

Source