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

HRID 1112247Notes

Reaction equation

HRID 1112247 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 1 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 1 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-b5140d623e9141cc8fb06329df6436fe
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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