Water → HCID 178507950, compound

HRID 850911Notes

Reaction equation

HRID 850911 reaction equation
[Na].[Cl:2][C:3]([Cl:8])([Cl:7])[C:4]([NH2:6])=[NH:5].[C:9]([CH2:11][C:12](OCC)=[O:13])#[N:10].O>CO.C(O)(=O)C>[NH2:10][C:9]1[N:6]=[C:4]([C:3]([Cl:8])([Cl:7])[Cl:2])[N:5]=[C:12]([OH:13])[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 356082,2,2-TrichloroethanimidamideHCID 5360545Sodium

Product 1

HCID 178507950HCID 178507950, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

To a solution of 5.8 g (0.025 g atom) sodium in 150 ml methanol at 15° C. was added 11.5 g (0.1 mole) trichloroacetamidine. To this was added 11.5 g (0.1 mole) ethyl cyanoacetate in 100 ml methanol. The solution was refluxed 1 hour and then the solvent was removed under rotary evaporation to give a red paste. This was dissolved in 20 ml warm water and 100 ml of 50% aqueous acetic acid was added, causing product to precipitate. Filtration, washing, and drying of the product gave 16.1 g (71% yield; mp 225°-230° C. (decomposed). The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperatureThe solution was refluxed 1 hour
  2. customthe solvent was removed under rotary evaporation
  3. customto give a red paste
  4. dissolutionThis was dissolved in 20 ml
  5. additionwas added
  6. customto precipitate
  7. filtrationFiltration
  8. washwashing
  9. customdrying of the product
  10. customgave 16.1 g (71% yield

Sources & evidence

ORD record
ord-7939540486004d22b7ba6bd0d95ce6bd
Source dataset
uspto-grants-1983_05
Patent number
US04382087

Reaction notes

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