Potassium Iodide → HCID 15279827, compound

HRID 2211268Notes

Reaction equation

HRID 2211268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]#[N:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:20][C:21]([CH2:23]Cl)=[CH2:22].[NH4+]=[S:26]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:23][C:21]([Cl:20])=[CH2:22])[C:10]([NH2:11])=[S:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 23279465(3,5-Dichlorophenyl)cyanamide

Product 1

HCID 15279827HCID 15279827, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

N-(3,5-dichlorophenyl)cyanamide (2.81 g) was dissolved in DMF (14.03 g), to which powdered potassium carbonate (3.11 g) and potassium iodide (0.26 g) were added at room temperature with stirring. Further, 2,3-dichloro-1-propene (2.00 g) was added dropwise at room temperature with stirring. The mixture was heated to 50° C. and stirred at the same temperature for 2.5 hours. After cooling to room temperature, DMF (9.00 g) and ammonium sulfide solution, yellow (8.00 g) having an S content of 6% were added dropwise to the reaction mixture at room temperature with stirring. The mixture was heated to 50° C. and stirred at the same temperature for 4 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 4.00 g of N-(3,5-dichlorophenyl)-N-(2-chloro-2-propenyl)thiourea as a dark red solid (90% yield in appearance). The percentage area of liquid chromatography was 94%.

Workup

  1. additionwere added at room temperature
  2. stirringwith stirring
  3. stirringstirred at the same temperature for 2.5 hours
  4. temperatureAfter cooling to room temperature
  5. additionwere added dropwise to the reaction mixture at room temperature
  6. stirringwith stirring
  7. temperatureThe mixture was heated to 50° C.
  8. stirringstirred at the same temperature for 4 hours
  9. temperatureAfter cooling to room temperature
  10. extractionwas then extracted with ethyl acetate
  11. washThe organic layer was washed with water
  12. customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record
ord-bab5536d565140eca65355d19d9d00d6
Source dataset
uspto-grants-1995_10
Patent number
US05463069

Reaction notes

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