Réaction #1442489

Équation de réaction

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

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
   AutreThe water was rotary evaporated
5. 5
   Lavagethe residue was washed with acetone
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe acetone washings were concentrated down
8. 8
   AutreA yellow solid was obtained
9. 9
   Autrerecrystallized with cold diethyl ether
10. 10
    Autreto give white crystals, m.p. 107-109.5° C

Mode opératoire

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