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

HRID 1283161Notes

Reaction equation

HRID 1283161 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-90325b22806e4779a67be3d1ba366287
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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