Hydrochloric Acid → Ethyl 3-ethoxy-3-iminopropionate hydrochloride

HRID 869452Notes

Reaction equation

HRID 869452 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[ClH:9].[CH2:10]([OH:12])[CH3:11]>C(Cl)(Cl)Cl>[ClH:9].[CH2:10]([O:12][C:1](=[NH:2])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7764Ethyl cyanoacetate

Product 1

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of ethyl 2-cyanoacetate (100 mL, 94 mmol) in chloroform (100 mL) and ethanol (6.5 mL) is bubbled with HCl at −10° for 4 h. The reaction mixture is allowed to warm to RT slowly and then stirred at RT overnight. The mixture is concentrated in vacuo to remove the solvent. The residue is suspended in diethyl ether (100 mL) and stirred for 30 min. The resulting solid is collected by filtration and rinsed with diethyl ether to afford ethyl 3-ethoxy-3-iminopropanoate hydrochloride (Z-1) as a white solid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customto remove the solvent
  3. stirringstirred for 30 min
  4. filtrationThe resulting solid is collected by filtration
  5. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-33072e2283794e65be612d8546cea0e6
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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