Cyanoacetamide → HCID 178429416, compound

HRID 574113Notes

Reaction equation

HRID 574113 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[C:7](OCC)(=[O:12])[CH2:8][C:9]([CH3:11])=O.[OH-].[K+]>CO>[C:1]([C:3]1[C:4]([OH:5])=[N:6][C:7]([OH:12])=[CH:8][C:9]=1[CH3:11])#[N:2]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8868Ethyl AcetoacetateHCID 14797Potassium Hydroxide

Product 1

HCID 178429416HCID 178429416, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Cyanoacetamide (8, 34 g, 0.40 mol) and ethyl acetoacetate (9, 52 g, 0.40 mol) were dissolved in methanol (250 mL) at room temperature, a solution of potassium hydroxide (28 g, 0.42 mol) in methanol (200 mL) was slowly added, and the resulting mixture was heated to reflux for 12 h. The reaction mixture was cooled to room temperature and the white amorphous precipitate was filtered and washed with methanol (2×50 mL). The solid product was redissolved in hot water. The solution was carefully acidified and the off-white precipitate was allowed to form. The precipitate was filtered and washed with water and methanol to yield 110 (46 g, 75%): mp>300° C. (dec) [lit. (J. Org. Chem. 1960, 25, 560-564.) mp 315-320° C. (dec)]. 1H NMR (300 MHz, DMSO-d6) δ 5.58 (s, 1H), 2.22 (s, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationthe white amorphous precipitate was filtered
  4. washwashed with methanol (2×50 mL)
  5. dissolutionThe solid product was redissolved in hot water
  6. customto form
  7. filtrationThe precipitate was filtered
  8. washwashed with water and methanol

Sources & evidence

ORD record
ord-96a07be2a8f1427f8fb03992185fa76a
Source dataset
uspto-grants-2015_05
Patent number
US09034870B2

Reaction notes

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