Cyanoacetic acid → 2-Cyano-N-[4-(trifluoromethyl)phenyl]acetamide

HRID 861543Notes

Reaction equation

HRID 861543 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([CH2:9][C:10]([OH:12])=O)#[N:8].[F:13][C:14]([F:23])([F:22])[C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[F:13][C:14]([F:22])([F:23])[C:15]1[CH:16]=[CH:17][C:18]([NH:19][C:10](=[O:12])[CH2:9][C:7]#[N:8])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 9740Cyanoacetic acidHCID 99644-(Trifluoromethyl)anilineHCID 10340Sodium CarbonateHCID 24819Phosphorus pentachloride

Product 1

HCID 38238032-Cyano-N-[4-(trifluoromethyl)phenyl]acetamideYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Phosphorus pentachloride (83.3 g; 0.40 mol) is introduced into a solution of cyanoacetic acid (34.0 g; 0.40 mol) in 1,2 l of dichloromethane and the mixture is heated under reflux for 30 minutes. 4-Trifluoromethylaniline (41.0 g, 0.26 mol) is then introduced into said mixture within about 10 minutes and the reaction mixture is heated under reflux for 2 hours. After cooling to 20° C., the reaction mixture is treated with 500 ml of water and then stirred for 30 minutes. The aqueous phase is neutralized with sodium carbonate and the precipitate is filtered off with suction. The filter cake is washed with water and dried. 55.2 g of N-(4-trifluoromethylphenyl)cyanoacetamide are thus obtained in crystalline form. Melting point: 194°-195.5° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. customwithin about 10 minutes
  4. temperaturethe reaction mixture is heated
  5. temperatureunder reflux for 2 hours
  6. filtrationthe precipitate is filtered off with suction
  7. washThe filter cake is washed with water
  8. customdried

Sources & evidence

ORD record
ord-0b36e0a3b5cb4432ba7bf00507c194b8
Source dataset
uspto-grants-1998_02
Patent number
US05714514

Reaction notes

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