Ethyl cyanoformate → HCID 54377216, compound

HRID 1657863Notes

Reaction equation

HRID 1657863 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:11]>>[CH2:8]([O:7][C:5]([C:4]1[N:11]([CH2:10][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=[N:2][N:1]=1)=[O:6])[CH3:9]

Participants

3

Reactant 2

HCID 69336Ethyl cyanoformateHCID 69480Acetic acid, azido-, ethyl ester

Product 1

HCID 54377216HCID 54377216, compound

Procedure

A mixture of ethyl azidoacetate (6.4 grams, 50 millimoles) and ethyl cyanoformate (distilled, 15.0 grams, 150 millimoles) was heated on a steam bath for 40 hours. The yellow reaction mixture was concentrated under vacuum to give 9.4 grams (83 percent of theoretical yield) of an oil. Distillation of a sample at 115°-117°C. (.015 mm.) gave a viscous oil. On standing the title product, as a crystalline solid, was obtained, m.p. 26°-29.5°C. The analysis was as follows:

Workup

  1. temperaturewas heated on a steam bath for 40 hours
  2. concentrationThe yellow reaction mixture was concentrated under vacuum
  3. customto give
  4. custom9.4 grams (83 percent of theoretical yield) of an oil
  5. distillationDistillation of a sample at 115°-117°C. (.015 mm.)
  6. customgave a viscous oil

Sources & evidence

ORD record
ord-5c922df139cd48c7b06feb6324c44c2b
Source dataset
uspto-grants-1976_06
Patent number
US03962272

Reaction notes

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