Ethyl cyanoformate → HCID 54377216, compound

HRID 1657866Notes

Reaction equation

HRID 1657866 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]>O1CCOCC1>[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

4

Reactant 2

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

Product 1

HCID 54377216HCID 54377216, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl azidoacetate (6.45 grams, 50 millimoles, 98.5 percent pure) and ethyl cyanoformate (10.0 grams, 100 millimoles) in 30 milliliters of dioxane was heated to reflux for 70 hours to insure complete reaction. The resulting reaction mixture was concentrated under vacuum to give 10.0 g. (88%) of the product as an oil. NMr indicated that the oil product was 88 percent pure; therefore, the actual yield from the reaction was 77 percent.

Workup

  1. temperatureto reflux for 70 hours
  2. customreaction
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated under vacuum
  5. customto give 10.0 g
  6. customtherefore, the actual yield from the reaction

Sources & evidence

ORD record
ord-51fbf948b51648feae4131e263763239
Source dataset
uspto-grants-1976_06
Patent number
US03962272

Reaction notes

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