Ethyl cyanoacetate → 2-cyano-N-(4-methylbenzyl)acetamide

HRID 436701Notes

Reaction equation

HRID 436701 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1>COCCO>[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 660354-Methylbenzylamine

Product 1

HCID 9033392-cyano-N-(4-methylbenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 93 g. (0.825 mole) of ethyl cyanoacetate and 100 g. (0.825 mole) of 4-methylbenzylamine in 150 ml. of 2-methoxyethanol is refluxed for 2 hr. After cooling the solid product is isolated by vacuum filtration, washed with pentane and dried to give 90 g. (57.6%) of amide as a white solid: m.p. 124°-6° C.; ν 3220 (NH), 2230 (CN), and 1630 cm.-1 (C=O) δ 8.77 broad, 1H, NH); 7.17 (s, 4H, phenyl protons), 4.28 (d, 2H, benzyl methylene), 3.67 (s, 2H, CH2CO), and 2.28 (s, 3H, CH3).

Workup

  1. temperatureAfter cooling the solid product
  2. customis isolated by vacuum filtration
  3. washwashed with pentane
  4. customdried
  5. customto give 90 g

Sources & evidence

ORD record
ord-1dc9e47af7dd4db8b708c359080e8de4
Source dataset
uspto-grants-1977_06
Patent number
US04028084

Reaction notes

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