N-Cyanoacetylethylcarbamate → ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

HRID 848692Notes

Reaction equation

HRID 848692 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10])=[O:5])[CH3:2].[CH2:12]([O:14][CH:15](OCC)OCC)[CH3:13]>C(OC(=O)C)(=O)C>[C:9]([C:8](=[CH:15][O:14][CH2:12][CH3:13])[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])#[N:10]

Participants

4

Reactant 2

HCID 23112N-CyanoacetylethylcarbamateHCID 31214Ethyl orthoformate

Product 1

HCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of N-ethoxycarbonylcyanoacetamide (42 g), triethylorthoformate (40 g) and acetic anhydride (100 ml) is heated at reflux for one hour. The reaction is allowed to stand until cool and then is filtered, washing with ether, to yield α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide.

Workup

  1. temperatureis heated
  2. temperatureat reflux for one hour
  3. temperatureuntil cool
  4. filtrationis filtered
  5. washwashing with ether

Sources & evidence

ORD record
ord-c15e5390453a4046b6a0903e8829e8f7
Source dataset
uspto-grants-1981_10
Patent number
US04297297

Reaction notes

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