Benzylamine → N-benzyl-2-cyanoacetamide

HRID 266706Notes

Reaction equation

HRID 266706 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C:12](OC)=[O:13])#[N:10]>>[CH2:1]([NH:8][C:12](=[O:13])[CH2:11][C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 7747Methyl cyanoacetate

Product 1

HCID 668298N-benzyl-2-cyanoacetamideYield 40%

Conditions

Temperature
100 °C

Procedure

To benzylamine (1.07 g, 0.01 mol) was added methyl cyanoacetate (0.99 g, 0.01 mol) and the mixture was heated for 16 h at 100° C. without condenser to allow evaporation of the methanol formed. Cooling gave a dark red solid which was triturated with ethanol, filtered and recrystallized from ethanol to give pure title compound in about 40% yield (0.70 g). mp 123°-4° C.

Workup

  1. customevaporation of the methanol
  2. customformed
  3. temperatureCooling
  4. customgave a dark red solid which
  5. customwas triturated with ethanol
  6. filtrationfiltered
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b5886fadbaac430d8e4a088ba8c1eeff
Source dataset
uspto-grants-1997_07
Patent number
US05652250

Reaction notes

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