Water → N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea

HRID 2292875Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:9]([CH2:12][C:13]([Cl:15])=[CH2:14])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.O.[NH4+]=[S:20]>C(C(C)=O)C(C)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([N:9]([CH2:12][C:13]([Cl:15])=[CH2:14])[C:10]([NH2:11])=[S:20])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)cyanamide (2.61 g) was dissolved in methyl isobutyl ketone (13.01 g), to which ammonium sulfide solution, yellow (8.12 g) having an S content of 6% was added dropwise at room temperature with stirring. The mixture was heated to 50° C. and stirred at the same temperature for 9 hours. After cooling to room temperature, water 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 2.67 g of N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea as a solid (90% yield in appearance). The percentage area of gas chromatography was 85%.

Workup

additionwas added dropwise at room temperature
stirringstirred at the same temperature for 9 hours
temperatureAfter cooling to room temperature
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-a07b06bf25ee4ac0be68a981ac058556
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05684196

Reaction notes

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