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

HRID 442207Notes

Reaction equation

HRID 442207 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-d3c8683c9ce841409698b4ab457b53e6
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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