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

HRID 1660161Notes

Reaction equation

HRID 1660161 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-ce1163e9f06b4b2cad154dcccf538134
Source dataset
uspto-grants-1981_12
Patent number
US04307098

Reaction notes

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