Hydrochloric Acid → Ethyl 2-hydroxypropanimidoate hydrochloride

HRID 1597192Notes

Reaction equation

HRID 1597192 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[OH:3].[ClH:6].[CH2:7]([O:9]CC)[CH3:8]>C(O)C>[ClH:6].[CH2:7]([O:9][C:1](=[NH:5])[CH:2]([OH:3])[CH3:4])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6572Lactonitrile

Product 1

HCID 86591879Ethyl 2-hydroxypropanimidoate hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (RS)-lactonitrile (378 9, 5.32 mol) in ethyl ether (1.46 L) and ethanol (0.34 L) was saturated with hydrogen chloride gas at 0° C.-5° C. for 0.5 h and kept at 5° C. for 60 h. The solid was filtered off and washed twice with ethyl ether to give 2-hydroxypropionimidic acid ethyl ester hydrochloride as a solid (815 g, 99%); mp, 165-168° C.; 1H NMR (DMSO-d6, 300 MHz) δ1.38 (t, 3H), 4.49(q, 1H), 6.55-7.11 (bs, 1H).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed twice with ethyl ether

Sources & evidence

ORD record
ord-e6c3712d4a3a49eb97de92fe21c27791
Source dataset
uspto-grants-2001_09
Patent number
US06294538B1

Reaction notes

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