Cyanoacetamide → HCID 178510367, compound

HRID 1953058Notes

Reaction equation

HRID 1953058 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=O)#[N:2].C[O-:8].[Na+].[CH3:10][N:11]([CH:13]=NC=[N+](C)C)C.[Cl-]>C(COC)OC>[C:1]([C:3]1[CH:10]=[N:11][C:13]([OH:8])=[N:6][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 11008255Gold's Reagent

Product 1

HCID 178510367HCID 178510367, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Cyanoacetamide (8.58 g, 0.10 mol) was added to an initial charge of sodium methoxide (54.02 g, 0.30 mol, 29% in methanol). 150 ml of dimethoxyethane were added. The solid Gold's reagent prepared as in Example 1 (18.08 g, 0.11 mol) was then added using a spatula. The suspension was then stirred overnight at room temperature. The yellow suspension was poured on to an aqueous, ice-cold hydrochloric acid solution (2 eq. of HCl) and adjusted to pH 5.5. After the organic solvents had been evaporated off, the product precipitated out of the aqueous phase. Digestion in water and subsequent filtration gave the title product in a yield of: 9.14 g (75%) in the form a yellow solid.

Workup

  1. additionwas then added
  2. customAfter the organic solvents had been evaporated off
  3. customthe product precipitated out of the aqueous phase
  4. filtrationDigestion in water and subsequent filtration

Sources & evidence

ORD record
ord-a2c99128f6c74b1f9a21e5ca732278a8
Source dataset
uspto-grants-2000_09
Patent number
US06114527

Reaction notes

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