Ethyl cyanoformate → HCID 54377216, compound

HRID 1657862Notes

Reaction equation

HRID 1657862 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, compoundYield 98%

Procedure

A mixture of ethyl azidoacetate (13.1 grams, 98.5 percent pure, 0.1 mole) and ethyl cyanoformate (20.0 grams, distilled, 0.2 mole) was heated in an oil bath at 110°-111°C. for 24 hours. Removal of excess ethyl cyanoformate in vacuo gave 22.25 grams (98% of theoretical yield) of ethyl 5-(ethoxycarbonyl)-1-H-tetrazole-1-acetate which was shown to be 91% pure by nuclear magnetic resonance.

Workup

  1. temperaturewas heated in an oil bath at 110°-111°C. for 24 hours
  2. customRemoval of excess ethyl cyanoformate in vacuo

Sources & evidence

ORD record
ord-b77760c7997048dd8df3a9e8af777c26
Source dataset
uspto-grants-1976_06
Patent number
US03962272

Reaction notes

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