Ethanol → N-(3,4-dichlorobenzyl)-2-cyanoacetamide

HRID 436700Notes

Reaction equation

HRID 436700 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:13][NH2:14].C(O)C>CCOCC>[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:13][NH:14][C:4](=[O:6])[CH2:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1608Benzenemethanamine, 3,4-dichloro-HCID 7764Ethyl cyanoacetate

Product 1

HCID 4168883N-(3,4-dichlorobenzyl)-2-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 113.3 g. (1.002 moles) of ethyl cyanoacetate and 176.4 g. (1.002 moles) of 3,4-dichlorobenzylamine in 400 ml. of absolute ethanol is heated at reflux with stirring for 42 hours which upon cooling the entire solution solidifies. The latter is broken-up, slurried in ether, isolated by filtration and dried in vacuo to give 179.8 g. of product as a white solid, m.p. 144°-5° C.

Workup

  1. temperatureat reflux
  2. temperatureupon cooling the entire solution
  3. customisolated by filtration
  4. customdried in vacuo
  5. customto give 179.8 g

Sources & evidence

ORD record
ord-aad702e175dd404bb99140aa581dbf31
Source dataset
uspto-grants-1977_06
Patent number
US04028084

Reaction notes

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