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

HRID 1378282Notes

Reaction equation

HRID 1378282 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].[CH2:10]([O:12][C:2](=[NH:3])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 7764Ethyl cyanoacetate

Product 1

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideYield 88%

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 below 15° C. by use of a cooling bath. After 3.5 hours 395 g (10.8 moles) of hydrogen chloride had been absorbed. The mixture was kept in a cold room for 72 hours. Then the resulting white, crystalline product was filtered off, washed first with diethyl ether, then with petroleum-ether (b.p. 60°-80° C.) and dried under vacuum. The product weighed 1210 g (88% yield).

Workup

  1. customThe temperature was kept below 15° C. by use of a cooling bath
  2. filtrationThen the resulting white, crystalline product was filtered off
  3. washwashed first with diethyl ether
  4. dry with materialwith petroleum-ether (b.p. 60°-80° C.) and dried under vacuum

Sources & evidence

ORD record
ord-b20376973a7b4b7eae4564c49208391e
Source dataset
uspto-grants-1997_09
Patent number
US05667946

Reaction notes

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