Ethylenediamine → HCID 2767072, compound

HRID 1448946Notes

Reaction equation

HRID 1448946 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].CO[CH:7]1[CH2:11][CH2:10][CH:9](OC)O1.[O:14]1CCO[CH2:16][CH2:15]1>C(O)(=O)C>[N:3]1([CH2:2][CH2:1][NH:4][C:15](=[O:14])[CH3:16])[CH:9]=[CH:10][CH:11]=[CH:7]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 312751,4-DioxaneHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2767072HCID 2767072, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethylenediamine (12 g), 2,5-dimethoxytetrahydrofuran (29 g), dioxane (400 ml), and acetic acid (200 ml) is refluxed for 4 hr and then stirred at 20° to 30° C. for 10 hr. The solvents are removed under reduced pressure, the residue is dissolved in chloroform and the solution is washed successively with conc. sodium bicarbonate and water. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue is crystallized from ethyl acetate-diethyl ether to give the title compound (20 g): mp 59°-60° C., ir(CHCl3) 3420 and 1660 cm-1, nmr-(CDCl3) δ 1.92(s), 3.25(dd), 3.62(dd), 3.99(dd), 4.06(dd), 6.00(s), 6.18(t) and 6.77(t), and anal. calc'd. for C8H12N2O: C, 63.13% H, 7.95% N, 18.41% and found: C, 63.27% H, 7.87% N, 18.51%.

Workup

  1. temperatureis refluxed for 4 hr
  2. customThe solvents are removed under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform
  4. washthe solution is washed successively with conc. sodium bicarbonate and water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-723d5b86de7844a5ab85d849a442871a
Source dataset
uspto-grants-1980_02
Patent number
US04188389

Reaction notes

Loading…