Potassium Iodide → HCID 15279831, compound

HRID 2211269Notes

Reaction equation

HRID 2211269 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]#[N:11])=[CH:5][CH:4]=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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:23][C:21]([Cl:20])=[CH2:22])[C:10]([NH2:11])=[S:26])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 1093158813519-16-9

Product 1

HCID 15279831HCID 15279831, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N-(4-methoxyphenyl)cyanamide (2.22 g) was dissolved in DMF (11.10 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 1.5 hours. After cooling to room temperature, ammonium sulfide solution, yellow (8.00 g) having an S content of 6% was added drop-wise to the reaction n-mixture at room temperature with stirring. The mixture was heated to 50° C. and stirred at the same temperature for 3 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 3.63 g of N-(4methoxyphenyl)-N-(2-chloro-2-propenyl)thiourea as a dark red solid (94% 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 1.5 hours
  4. temperatureAfter cooling to room temperature
  5. additionwas added drop-wise
  6. customto the reaction n-mixture at room temperature
  7. stirringwith stirring
  8. temperatureThe mixture was heated to 50° C.
  9. stirringstirred at the same temperature for 3 hours
  10. temperatureAfter cooling to room temperature
  11. extractionwas then extracted with ethyl acetate
  12. washThe organic layer was washed with water
  13. customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record
ord-69796e37d5bc4a11a7de0cef3f3bb5bf
Source dataset
uspto-grants-1995_10
Patent number
US05463069

Reaction notes

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