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

HRID 544193Notes

Reaction equation

HRID 544193 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-5c80c8f8c9c545f4b671993dcdcb6e77
Source dataset
uspto-grants-1984_05
Patent number
US04448961

Reaction notes

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