Acetic Acid → ethyl (2E)-3-amino-3-[bis(2,4-dimethoxybenzyl)amino]prop-2-enoate

HRID 570711Notes

Reaction equation

HRID 570711 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[O:16][CH3:17].C(O[C:27](=[NH:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])C.C(O)(=O)C>C(O)C>[NH2:34]/[C:27](/[N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[O:16][CH3:17])[CH2:5][C:4]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:3]=1[O:2][CH3:1])=[CH:28]\[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl esterHCID 88696Bis(2,4-dimethoxybenzyl)amine

Product 1

HCID 86685371ethyl (2E)-3-amino-3-[bis(2,4-dimethoxybenzyl)amino]prop-2-enoateYield 156.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of bis(2,4-dimethoxybenzyl)amine (8 g), ethyl 3-ethoxy-3-iminopropanoate (8.02 g), acetic acid (1.44 mL) and ethanol (420 mL) was refluxed overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (17 g).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-25f6f8b84c8e48d2bbfce6c8e618e59a
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

Loading…