Triethylenetetramine → HCID 18506312, compound

HRID 1355308Notes

Reaction equation

HRID 1355308 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:15])[C:12]([CH3:14])=[CH2:13].[K+].[Br-]>ClCCl>[C:11]([C:2]([C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])([CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10])[N:1]([C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])[C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

5

Reactant 3

HCID 5565TriethylenetetramineHCID 13528Methacryloyl chlorideHCID 253877Potassium Bromide

Product 1

HCID 18506312HCID 18506312, 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 methacryloyl chloride (8.32 g, 0.08 moles) in dichloromethane (40 ml), stirring vigorously at room temperature. The reaction was continued stirring at room temperature overnight and the suspension formed 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 filtrate was concentrated down and put through a silica gravity chromatography column with acetone as the elutant to obtain a white solid. The solid is recrystallized from diethyl ether to give white crystals, m.p. 168-170° C. 1H n.m.r. (D2O) δ, 5.71(19.7 Hz), 5.51 (7.8 Hz), 5.31(9.7 Hz), 5.06 (17.7 Hz), (8 H, d×4) C—CH2; 3.61 (6 H, m) N—CH2—CH2; 3.48(6 H, m) N—CH2—CH2; 1.96(4.1 Hz); 1.93(5.8 Hz); 1.91(6.0 Hz); 1.88(4.5 Hz), (12 H, d×4) CH3; 13C n.m.r. (D2O), δ 178.76, 178.70, 174.71, 174.61 (C=O); 142.19, 142.0, 141.71, 141.56 (C=CH2), 124.52, 124.19, 120.06, 119.60 (C=CH2); 22.30, 22.20, 20.48; (CH3), 50.33, 49.22, 46.45, 44.00, 40.22, 39.49 (N—CH2—CH2). MS: mz: 419.3 (MH+, 100%), 391.3(4), 266.2(10), 223.1(42); HRMS: found: 419.26695 C22H34N4O4 requires 418.5299. Elemental analysis: found: C, 62.97; H, 8.09; N, 13.31; C22H34N4O4 requires C, 63.13; H, 8.19; N, 13.39. I.R. (KBr) (CM−1) 3353, 1665, 1650, 1530, 1279.

Workup

  1. stirringThe reaction was continued stirring at room temperature overnight
  2. customthe suspension formed
  3. filtrationwas filtered
  4. extractionThe filtrate was extracted with NaOH (aq)
  5. customThe water was rotary evaporated
  6. washthe residue was washed with acetone
  7. filtrationfiltered
  8. concentrationThe acetone filtrate was concentrated down
  9. customto obtain a white solid
  10. customThe solid is recrystallized from diethyl ether
  11. customto give white crystals, m.p. 168-170° C

Sources & evidence

ORD record
ord-697730dd1f5743999dd5e53ecfb10324
Source dataset
uspto-grants-2003_07
Patent number
US06585873B1

Reaction notes

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