Sulfuric Acid → HCID 86623120, compound

HRID 548784Notes

Reaction equation

HRID 548784 reaction equation
[CH2:1]([O:3][CH:4]([CH3:7])[CH2:5][NH2:6])[CH3:2].C([N:16]=[C:17]=[S:18])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[CH2:1]([O:3][CH:4]([CH3:7])[CH2:5][NH:6][C:17]([NH2:16])=[S:18])[CH3:2]

Participants

6

Conditions

Temperature
75 °C

Procedure

2-Ethoxy-propylamine (1.50 g, 14.5 mmol) and benzoylisothiocyanate (2.61 g, 16.0 mmol) in chloroform (50 mL) were heated at 75° C. for 1 h. The solvent was removed under reduced pressure and methanol (15 mL) and water (30 mL) were added. Potassium carbonate (2.0 g, 14.5 mmol) was added and the mixture was heated at 75° C. for 2 h. After cooling to room temperature, the mixture was neutralized with 2M sulphuric acid and the solvent was removed under reduced pressure. The crude product was dissolved in methanol and insoluble material was removed by filtration. The solvent was distilled off and the resulting solid was washed with dichloromethane and dissolved in ethanol. Insoluble material was removed by filtration and the solvent was removed under reduced pressure. This gave the title compound as a white solid (1.6 g, 59% yield).

Workup

  1. customThe solvent was removed under reduced pressure and methanol (15 mL) and water (30 mL)
  2. additionwere added
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe crude product was dissolved in methanol
  6. custominsoluble material was removed by filtration
  7. distillationThe solvent was distilled off
  8. washthe resulting solid was washed with dichloromethane
  9. dissolutiondissolved in ethanol
  10. customInsoluble material was removed by filtration
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fe498ca40f2543dd80ffe58a0d6c2ed6
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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