Cyanoacetic acid → HCID 19076040, compound

HRID 1289280Notes

Reaction equation

HRID 1289280 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[NH2:17]>ClCCl>[C:1]([CH2:3][C:4]([NH:17][C:16]1[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:14]([CH3:13])[CH:15]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 118984-Nitro-m-toluidineHCID 24819Phosphorus pentachloride

Product 1

HCID 19076040HCID 19076040, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanoacetic acid (1.5 g; 17.6 mmol) and phosphorus pentachloride (4.1 g; 19.4 mmol) are heated under reflux in dichloromethane (40 ml) for 1 hour. 3-Methyl-4-nitroaniline (1.6 g; 10.6 mmol) is added and the mixture is heated for a further hour under reflux conditions. After cooling, the solid is filtered and stirred with water for a further hour, the mixture is filtered and the filtrate is brought to dryness under reduced pressure. 2-Cyano-N-(3-methyl-4-nitrophenyl)acetamide (1.4 g; 64%) is thus obtained.

Workup

  1. temperaturethe mixture is heated for a further hour under reflux conditions
  2. temperatureAfter cooling
  3. filtrationthe solid is filtered
  4. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-10fff33d9ab5402681860c887c6152e3
Source dataset
uspto-grants-1998_05
Patent number
US05747664

Reaction notes

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