Hydrochloric Acid → Ethyl 2-ethoxy-2-iminoacetate hydrochloride

HRID 1493683Notes

Reaction equation

HRID 1493683 reaction equation
[ClH:1].[CH2:2]([O:4]CC)[CH3:3].[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:8]>C(O)C>[ClH:1].[CH2:12]([O:11][C:9]([C:7](=[NH:8])[O:4][CH2:2][CH3:3])=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69336Ethyl cyanoformate

Product 1

HCID 12773119Ethyl 2-ethoxy-2-iminoacetate hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A hydrogen chloride gas was introduced into a diethyl ether solution of an equimolar mixture of ethyl cyanoformate and ethanol at 0° C. or lower, and a precipitated crystal was filtered out and washed with diethyl ether to obtain ethyl ethoxycarbonylformimidate hydrochloride [H5C2O2CC(OC2H5)=NH.HCl]. 5.4 g of this hydrochloride, 40 ml of acetic acid, 5.0 g of phenacylamine hydrochloride (the same as used in Synthesis Example 2) and 4.85 g of anhydrous sodium acetate were mixed and reacted with stirring at 90° to 100° C. for 4 hours.

Workup

  1. filtrationlower, and a precipitated crystal was filtered out
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-79bd3648fd2843c9a90d9bba5185f926
Source dataset
uspto-grants-1991_06
Patent number
US05023336

Reaction notes

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