Ethanolamine → N-(2-Hydroxyethyl)-2,2-dimethylpropanamide

HRID 1916342Notes

Reaction equation

HRID 1916342 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[OH-].[K+].[C:7](Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]>O>[OH:2][CH2:1][CH2:3][NH:4][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14797Potassium HydroxideHCID 62493Pivaloyl chloride

Product 1

HCID 15074197N-(2-Hydroxyethyl)-2,2-dimethylpropanamideYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred 4° aqueous solution containing ethanolamine (610 mg, 10 mmol), KOH (840 mg, 15 mmol) and H2O (15 mL) was added pivaloyl chloride (1.44 g, 12 mmol) whereupon the reaction was allowed to slowly warm to 20°. After stirring for 18 hr, the solution was extracted 4× with EtOAc,. The combined organic layers were washed with brine, dried over Na2SO4 prior to concentration using a rotary evaporator to yield 737 mg of a clear oil.

Workup

  1. temperatureto slowly warm to 20°
  2. extractionthe solution was extracted 4× with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationto concentration
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-eb83732cd0b04f12ab314b4768a224b3
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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