Ethylenediamine → HCID 86624946, compound

HRID 913382Notes

Reaction equation

HRID 913382 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.C[O:13][C:14](=O)[CH2:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18].C(N)CN>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:18][CH:17]([CH3:19])[C:16](=[O:20])[CH2:15][C:14]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][CH:6]=1)=[O:13]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 12082Methyl 4-aminobenzoateHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 86624946HCID 86624946, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl-4-aminobenzoate (250 g, 1.65 moles) in toluene (2.4 L) was added methyl-4-methyl-3-oxopentanoate (237.7 g, 1.648 moles) and ethylene diamine (1.15 ml, 0.016 moles). The reaction mixture was refluxed for about 20-25 hours. The solvent was removed under reduced pressure to obtain a solid residue. The residue was dissolved in ethyl acetate (2.4 L). The organic phase was washed with an acid (e.g., 20% w/w hydrochloric acid 0.5 L) followed by de-ionized water. It was further washed with a 10% sodium bicarbonate solution, followed by de-ionized water and saturated brine. The solvent was removed under reduced pressure. To this was added hexane while stirring and the solid precipitated out completely. The solid was filtered and washed with hexane. The solid was dried to yield the title product in 99.45% purity.

Workup

  1. temperatureThe reaction mixture was refluxed for about 20-25 hours
  2. customThe solvent was removed under reduced pressure
  3. customto obtain a solid residue
  4. washThe organic phase was washed with an acid (e.g., 20% w/w hydrochloric acid 0.5 L)
  5. washIt was further washed with a 10% sodium bicarbonate solution
  6. customThe solvent was removed under reduced pressure
  7. additionTo this was added hexane
  8. customthe solid precipitated out completely
  9. filtrationThe solid was filtered
  10. washwashed with hexane
  11. customThe solid was dried

Sources & evidence

ORD record
ord-7cd1604a83424c3faef24925e015c8fc
Source dataset
uspto-grants-2011_09
Patent number
US08026377B2

Reaction notes

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