Methyl Acrylate → HCID 22737591, compound

HRID 861294Notes

Reaction equation

HRID 861294 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]>C(#N)C>[CH3:17][O:16][C:12](=[O:15])[CH2:13][CH2:14][NH:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 7294Methyl Acrylate2×HCID 187201N-BOC-ethylenediamine

Product 1

HCID 22737591HCID 22737591, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Mono-BOC-ethylenediamine (2) (16.28 g, 0.102 mol) was dissolved in acetonitrile (400 mL) and methyl acrylate (91.5 mL, 1.02 mol) was transferred to the mixture with acetonitrile (200 mL). The solution was refluxed overnight under nitrogen in the dark to avoid polymerization of methyl acrylate. After evaporation to dryness in vacuo, a mixture of water and ether (200 mL+200 mL) was added, and the solution was filtered and vigorously stirred. The aqueous phase was extracted one additional time with ether and then freeze dried to yield a yellow solid. Recrystallization from ethyl acetate yielded 13.09 g (46%) of the title compound. M.p. 138°-140° C. Anal. for C11H23 N2O4Cl, found (calc.) C: 46.49 (46.72) H: 8.38 (8.20) N: 9.83 (9.91) Cl: 12.45 (12.54). 1H-NMR (90 MHz; DMSO-d6) δ: 1.39 (s, 9H); 2.9 (m, 8H); 3.64 (s, 3H).

Workup

  1. temperatureThe solution was refluxed overnight under nitrogen in the dark
  2. customAfter evaporation to dryness in vacuo
  3. additiona mixture of water and ether (200 mL+200 mL)
  4. additionwas added
  5. filtrationthe solution was filtered
  6. extractionThe aqueous phase was extracted one additional time with ether
  7. customfreeze dried
  8. customto yield a yellow solid
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8339886e4bf44bf983bcac7ae5f4c013
Source dataset
uspto-grants-1998_02
Patent number
US05714331

Reaction notes

Loading…