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

HRID 2211267Notes

Reaction equation

HRID 2211267 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

4

Reactant 2

HCID 962WaterHCID 21480055N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)cyanamide

Product 1

HCID 11130193N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thioureaYield 90%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

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

  1. additionwas added dropwise at room temperature
  2. stirringstirred at the same temperature for 9 hours
  3. temperatureAfter cooling to room temperature
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record
ord-ff479b2a852e4217a442d43cef1b917f
Source dataset
uspto-grants-1995_10
Patent number
US05463069

Reaction notes

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