Ethanol → Ethyl 2-(ethylamino)acetate

HRID 2207064Notes

Reaction equation

HRID 2207064 reaction equation
S(=O)(=O)(O)O.[CH2:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH3:7].[OH-].[Na+].C(=O)([O-])O.[Na+].[CH3:20][CH2:21]O>>[CH2:6]([NH:8][CH2:9][C:10]([O:12][CH2:20][CH3:21])=[O:11])[CH3:7]

Participants

6

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 316542N-EthylglycineHCID 516892Sodium Bicarbonate

Product 1

HCID 12591597Ethyl 2-(ethylamino)acetate

Procedure

Sulfuric acid (3 mL) was added to a solution of N-ethylglycine (2.0 g) in EtOH (15 mL) and the mixture was stirred under reflux for 9 h. The mixture was cooled to RT and neutralized with 5M-sodium hydroxide, and saturated aqueous sodium hydrogen carbonate. The solution was extracted with EtOAc, the combined organic layer was washed with brine, dried and concentrated under reduced pressure. The sub-title compound (1.4 g) was obtained as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 4.17 (2H, q), 3.38 (2H, s), 2.63 (2H, q), 1.25 (3H, t), 1.10 (3H, t).

Workup

  1. temperatureunder reflux for 9 h
  2. extractionThe solution was extracted with EtOAc
  3. washthe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba277b764d7e4d46ae1156b92894843d
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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