Cyanoacetamide → HCID 54540913, compound

HRID 614891Notes

Reaction equation

HRID 614891 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C([C:9](CC)(CC)[C:10]([O-:13])([O-])[O-])C.[NH:18]1[CH2:23][CH2:22]O[CH2:20][CH2:19]1>C(#N)C>[CH3:20][C:19]([N:18]1[CH2:9][CH2:10][O:13][CH2:22][CH2:23]1)=[C:3]([C:1]#[N:2])[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8083MorpholineHCID 21875354Triethylorthoaceate

Product 1

HCID 54540913HCID 54540913, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of cyanoacetamide (84 g.), triethylorthoacetate (178 g.) and morpholine (108 g.) was heated under reflux for 3 hours. The initial reflux temperature was 104° C. and the final reflux temperature was 89° C. At the end of the reflux period acetonitrile (50 ml.) was added, the mixture was cooled at 25° C., the crystalline precipitate was collected, and washed with 2 × 100 ml. of cold ethanol. Weight = 104.7 g. Yield = 53%. A sample was recrystallized from ethanol as white needles m.p. 173°-174.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe initial reflux temperature
  4. customwas 104° C.
  5. temperaturethe final reflux temperature
  6. customwas 89° 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. 173°-174.5° C.

Sources & evidence

ORD record
ord-ad227bd7f02449c996a383a40b077af0
Source dataset
uspto-grants-1979_03
Patent number
US04146713

Reaction notes

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