Ethylenediamine → 1,4,8,11-Tetraazacyclotetradecane-5,12-dione

HRID 745742Notes

Reaction equation

HRID 745742 reaction equation
[C:1]([O:5]C)(=O)[CH:2]=[CH2:3].[CH2:7]([NH2:10])[CH2:8][NH2:9].C[O:12][C:13](=O)[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][NH2:19]>O>[NH:9]1[CH2:3][CH2:2][C:1](=[O:5])[NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][C:13](=[O:12])[NH:10][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 7294Methyl AcrylateHCID 13647417HCID 13647417, compound

Product 1

HCID 63892701,4,8,11-Tetraazacyclotetradecane-5,12-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl acrylate (344 g, 4.0 moles) was added dropwise into neat ethylenediamine (240 g, 4.0 moles) while stirring. Addition was conducted at such a rate that the reaction temperature did not exceed 45° C. Addition time was 4.0 hours. The crude colorless product, N-(2-aminoethyl)-β-alanine methyl ester (580 g), was dissolved in deionized water to give a concentration of about 25 weight percent. Allowing the solution to stand at room temperature for 2-3 days caused a white solid product to slowly precipitate. The product was obtained as a fine white powder, m.p. 198° C.-199° C. Spectral analysis confirmed the product's structure as

Workup

  1. additionAddition
  2. customdid not exceed 45° C
  3. additionAddition time
  4. customto give a concentration of about 25 weight percent
  5. waitto stand at room temperature for 2-3 days
  6. customto slowly precipitate
  7. customThe product was obtained as a fine white powder, m.p. 198° C.-199° C

Sources & evidence

ORD record
ord-414d205e065847e88c4793c980bc0c6c
Source dataset
uspto-grants-1986_07
Patent number
US04600535

Reaction notes

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