Cyanoacetamide → alpha-Cyano-beta-(2-Nitro-5-Chlorophenyl)Acrylamide

HRID 2163582Notes

Reaction equation

HRID 2163582 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].C(NCC)C.[O-]CC.[Na+]>C(O)C>[C:13]([C:15](=[CH:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])[C:16]([NH2:18])=[O:17])#[N:14]

Participants

6

Reactant 4

HCID 7898CyanoacetamideHCID 8021DiethylamineHCID 811235-Chloro-2-nitrobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 54133839alpha-Cyano-beta-(2-Nitro-5-Chlorophenyl)Acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chloro-2-nitrobenzaldehyde (47.0 g., 0.25 mole), 2-cyanoacetamide (21.0 g., 0.25 mole), diethylamine (0.5 ml.) and ethanol (500 ml) is heated at reflux for one hour. Sodium ethoxide (10 mg.) is added to the clear mixture and refluxing continued for an additional 2.5 hours. It is then cooled and the crystalline product which precipitates recovered by filtration. Yield = 52.3 g. (88%); m.p. of crude = 183°-185° C. It is used without purification in step B.

Workup

  1. temperatureis heated
  2. temperatureat reflux for one hour
  3. temperaturerefluxing
  4. temperatureIt is then cooled
  5. customthe crystalline product which precipitates
  6. filtrationrecovered by filtration
  7. customm.p. of crude = 183°-185° C
  8. customIt is used without purification in step B

Sources & evidence

ORD record
ord-4270302f65a34cbe91e6c9326e710634
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Reaction notes

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