Ethanolamine → 2-cyano-N-(2-hydroxyethyl)acetamide

HRID 1162775Notes

Reaction equation

HRID 1162775 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[NH2:9][CH2:10][CH2:11][OH:12]>CCO>[C:1]([CH2:3][C:4]([NH:9][CH2:10][CH2:11][OH:12])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7764Ethyl cyanoacetate

Product 1

HCID 51527282-cyano-N-(2-hydroxyethyl)acetamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-cyanoacetate (10 g, 9.41 mL, 88 mmol) in EtOH (100 mL) was added 2-aminoethanol (5.40 g, 5.34 mL, 88 mmol). The mixture was refluxed for 4 h before concentration in vacuo. The mixture was purified on a 100 g Silica column eluting with 0-10% MeOH/DCM. Desired fractions were collected and concentrated to yield the desired product as a brown oil (10.2 g, 79.7 mmol, 90%). The sample was used directly in the next step without any further purification.

Workup

  1. temperatureThe mixture was refluxed for 4 h before concentration in vacuo
  2. customThe mixture was purified on a 100 g Silica column
  3. washeluting with 0-10% MeOH/DCM
  4. customDesired fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7b7e49656ed48e390980ec8e9afd00f
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

Loading…