Triethylenetetramine → HCID 90928894, compound

HRID 1355307Notes

Reaction equation

HRID 1355307 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].[K+].[Br-]>ClCCl>[C:11]([C:2]([C:11](=[O:14])[CH:12]=[CH2:13])([CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10])[N:1]([C:11](=[O:14])[CH:12]=[CH2:13])[C:11](=[O:14])[CH:12]=[CH2:13])(=[O:14])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 5565TriethylenetetramineHCID 13140Acryloyl chlorideHCID 253877Potassium Bromide

Product 1

HCID 90928894HCID 90928894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. filtrationthe suspension was filtered
  3. extractionThe filtrate was extracted with NaOH(aq)
  4. customThe water was rotary evaporated
  5. washthe residue was washed with acetone
  6. filtrationfiltered
  7. concentrationThe acetone washings were concentrated down
  8. customA yellow solid was obtained
  9. customrecrystallized with cold diethyl ether
  10. customto give white crystals, m.p. 107-109.5° C

Sources & evidence

ORD record
ord-4969ae708dcd4389a32f065947f4782a
Source dataset
uspto-grants-2003_07
Patent number
US06585873B1

Reaction notes

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