Reacción #1442489

Ecuación de reacción

Triethylene tetramine

acryloyl chloride

KBr

→

Tetra acryloyl triethylene tetramine

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature overnight
2. 2
   Filtraciónthe suspension was filtered
3. 3
   ExtracciónThe filtrate was extracted with NaOH(aq)
4. 4
   OtroThe water was rotary evaporated
5. 5
   Lavadothe residue was washed with acetone
6. 6
   Filtraciónfiltered
7. 7
   ConcentraciónThe acetone washings were concentrated down
8. 8
   OtroA yellow solid was obtained
9. 9
   Otrorecrystallized with cold diethyl ether
10. 10
    Otroto give white crystals, m.p. 107-109.5° C

Procedimiento

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.

Fuente