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

HRID 2286436Notes

Reaction equation

HRID 2286436 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 to 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. temperatureto reflux for one hour
  3. temperatureuntil cool
  4. filtrationis filtered
  5. washwashing with ether

Sources & evidence

ORD record
ord-97bf22f4829e469095bce30c708399da
Source dataset
uspto-grants-1981_05
Patent number
US04266056

Reaction notes

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