Ethyl cyanoacetate → HCID 964628, compound

HRID 436697Notes

Reaction equation

HRID 436697 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH2:13]>C(O)C>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH:13][C:4](=[O:6])[CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 666482-Chlorobenzylamine

Product 1

HCID 964628HCID 964628, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.;ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C=O);δ8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent is removed in vacuo
  3. customthe residue is recrystallized from ether/pentane
  4. customto give 56 g

Sources & evidence

ORD record
ord-64b6f6c055f349e0a67860281b62bdfc
Source dataset
uspto-grants-1977_06
Patent number
US04028084

Reaction notes

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