Potassium Iodide → N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)cyanamide

HRID 2292874Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([NH:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:22][C:23]([CH2:25]Cl)=[CH2:24]>CN(C)C=O>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([N:9]([CH2:25][C:23]([Cl:22])=[CH2:24])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

N-(3-(trifluoromethyl)phenyl)cyanamide (18.6 g) was dissolved in N,N-dimethylformamide (DMF) (93.0 g), to which powdered potassium carbonate (20.7 g) and potassium iodide (1.7 g) were added at room temperature with stirring. Further, 2,3-dichloro-1-propene (13.3 g) was added dropwise at room temperature with stirring. The mixture was heated to 50° C. and stirred at the same temperature for 1 hour. After cooling to room temperature, waster was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, which afforded 25.8 g of N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)cyanamide as an oil (99% yield in appearance). The percentage areas of gas chromatography and liquid chromatography were 98% and 99%, respectively.

Workup

additionwere added at room temperature
stirringwith stirring
stirringstirred at the same temperature for 1 hour
temperatureAfter cooling to room temperature
additionwaster was added to the reaction mixture, which
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with water
customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record: ord-2f00ef87aadc412c88c76f096b71d7e0
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05684196

Reaction notes

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