Ammonia → 4-(Trifluoromethyl)-cinnamamide

HRID 352068Notes

Reaction equation

HRID 352068 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH3:20]>C1(C)C=CC=CC=1.CN(C)C=O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([NH2:20])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Product 1

HCID 27790124-(Trifluoromethyl)-cinnamamideYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

4-(Trifluoromethyl)cinnamic acid (64.85 g, 300 mmol) was added in toluene (325 ml) and dimethylformamide (2.2 ml). Thionyl chloride (26.3 ml, 361 mmol) was added dropwise at room temperature, and the mixture was heated at 45° C. for 2 hours. The obtained reaction mixture was added dropwise to 25% aqueous ammonia (325 ml) while keeping the mixture at 5-20° C. The mixture was stirred at room temperature for 1 hour. The precipitated crystals were collected by filtration, washed with 20 water and isopropyl ether and dried under reduced pressure to give 4-(trifluoromethyl)cinnamamide (60.76 g, yield 94%).

Workup

  1. customThe obtained reaction mixture
  2. customat 5-20° C
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with 20 water and isopropyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-de84aa3f8f004885984255ba209619f0
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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