Ethyl cyanoacetate → 2-cyano-N-(prop-2-yn-1-yl)acetamide

HRID 2228348Notes

Reaction equation

HRID 2228348 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].CCO[C:8]([CH2:10][C:11]#[N:12])=[O:9]>>[C:11]([CH2:10][C:8]([NH:4][CH2:1][C:2]#[CH:3])=[O:9])#[N:12]

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 239041Propargylamine

Product 1

HCID 184695792-cyano-N-(prop-2-yn-1-yl)acetamideYield 94.2%

Procedure

A mixture of 15.4 ml (240 mmol) of propargyl amine and 17.1 ml (160 mmol) of ethyl cyano acetate was heated for 7 hours to 40° C. in a reaction flask. The crystalline material formed was heated for another 17 hours to 70° C. Then, the cooled reddish product was dried at high vacuum to yield 18.4 g (94%) of a red powder, m.p. 100-103° C.

Workup

  1. temperaturewas heated for 7 hours to 40° C. in a reaction flask
  2. customThe crystalline material formed
  3. temperaturewas heated for another 17 hours to 70° C
  4. customThen, the cooled reddish product was dried at high vacuum

Sources & evidence

ORD record
ord-eb07bdf180aa4aa5a3552ea2a0944690
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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