Aminoacetonitrile → n-(Cyanomethyl)-3-oxobutanamide

HRID 372825Notes

Reaction equation

HRID 372825 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][C:9]#[N:10]>CO>[C:8]([CH2:9][NH:10][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])#[N:7]

Participants

4

Reactant 2

HCID 10901AminoacetonitrileHCID 12661Diketene

Product 1

HCID 225301n-(Cyanomethyl)-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

While stirring at -10° to 0° C, 92 g of freshly distilled diketene are added dropwise to a solution of 400 ml of methanol and 56 g of freshly distilled aminoacetonitrile. The mixture is allowed to warm to room temperature and stirring is continued for 2 hours at 35° C in a water bath. The solvent is distilled off by rotary evaporation and the solid residue is suspended in cold ether. Suction filtration yields the colourless, crystalline, pure acetoacetic N-cyanomethylamide with a melting point of 63°-65° C.

Workup

  1. stirringstirring
  2. distillationThe solvent is distilled off by rotary evaporation
  3. filtrationSuction filtration

Sources & evidence

ORD record
ord-edf8403fec024ca0b4dada8603fe6c81
Source dataset
uspto-grants-1978_05
Patent number
US04092415

Reaction notes

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