Diethyl Ether → Ethyl 2-Aminobutyrate Hydrochloride

HRID 848

Reaction equation

HRID 848 reaction equation
[NH2:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].S(Cl)([Cl:10])=O.[CH2:12](OCC)[CH3:13]>C(O)C>[ClH:10].[NH2:1][CH:2]([CH2:6][CH3:7])[C:3]([O:5][CH2:12][CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6657Alpha-Aminobutyric AcidHCID 24386Thionyl Chloride

Product 1

HCID 12844023Ethyl 2-Aminobutyrate Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 2-aminobutyric acid (100 g, Aldrich) in absolute ethanol (300 ml) was stirred under nitrogen at 0° C. and thionyl chloride (120.8 g) was added dropwise. The reaction was stirred overnight at 0° C. and then gradually warmed to room temperature. The resulting white slurry was heated under reflux for 3 hours, left to cool for 10 minutes, then poured into chilled diethyl ether (600 ml), with hand stirring. The suspension was filtered and the solid product dried to give the desired product (150 g) as a white solid. 1H NMR consistent with proposed structure.

Workup

  1. temperaturegradually warmed to room temperature
  2. temperatureThe resulting white slurry was heated
  3. temperatureunder reflux for 3 hours
  4. waitleft
  5. temperatureto cool for 10 minutes
  6. additionpoured
  7. stirringwith hand stirring
  8. filtrationThe suspension was filtered
  9. customthe solid product dried

Sources & evidence

ORD record
ord-57d496f8cfa74e14b0b60ed9b08a5969
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

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