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

HRID 2226819Notes

Reaction equation

HRID 2226819 reaction equation
[ClH:1].[C:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3].[CH2:10]([OH:12])[CH3:11]>C(OCC)C>[ClH:1].[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C:2]([O:12][CH2:10][CH3:11])=[NH:3])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 7764Ethyl cyanoacetate

Product 1

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrogen chloride gas was bubbled through a stirred solution of ethyl cyanoacetate (900 g, 7.96 moles), ethanol (410 ml, 7.0 moles) and diethyl ether (2.4 liters). The temperature was kept at <15° C. by use of a cooling bath. After 3.5 hours 395 g (10.8 moles) of HCl had been absorbed. The flask was kept in the cold room over the weekend. The crystalline white product was filtered off, washed with diethyl ether, then petroleum ether and dried under vacuum. The yield was 1210 g (88% ).

Workup

  1. customThe temperature was kept at <15° C. by use of a cooling bath
  2. filtrationThe crystalline white product was filtered off
  3. washwashed with diethyl ether
  4. dry with materialpetroleum ether and dried under vacuum

Sources & evidence

ORD record
ord-f9f0eab0239f4b4bba3726ab1a395d58
Source dataset
uspto-grants-1994_09
Patent number
US05350667

Reaction notes

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