Cyanoacetamide → HCID 54297024, compound

HRID 614892Notes

Reaction equation

HRID 614892 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C(O[C:10](OCC)(OCC)[CH2:11][CH3:12])C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(#N)C>[CH2:11]([C:12]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[C:3]([C:1]#[N:2])[C:4]([NH2:6])=[O:5])[CH3:10]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8083MorpholineHCID 66995Ethyl orthopropionate

Product 1

HCID 54297024HCID 54297024, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of cyanoacetamide (84 g.), triethylorthopropionate (193 g.) and morpholine (108 g.) was heated under reflux for 3 hours. The initial reflux temperature was 121° C. and the final reflux temperature was 91° C. At the end of the reflux period acetonitrile (50 ml.) was added, the mixture was cooled to 25° C., the crystalline precipitate was collected, and washed with 2 × 100 ml. of cold ethanol. Weight = 87 g. Yield = 42%. A sample was recrystallized from ethanol as white needles m.p. 158° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe initial reflux temperature
  4. customwas 121° C.
  5. temperaturethe final reflux temperature
  6. customwas 91° C
  7. customthe crystalline precipitate was collected
  8. washwashed with 2 × 100 ml
  9. customA sample was recrystallized from ethanol as white needles m.p. 158° C.

Sources & evidence

ORD record
ord-e6d3211c5f5442b392b9212eec57845d
Source dataset
uspto-grants-1979_03
Patent number
US04146713

Reaction notes

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