Methyl iodide → HCID 22288810, compound

HRID 968298Notes

Reaction equation

HRID 968298 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])=S.CI>C(O)C>[ClH:19].[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[NH:12][C:10]1[NH:9][C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22288818N-(2-Amino-5-fluorophenyl)-N′-(2,6-dichlorophenyl)thiourea

Product 1

HCID 22288810HCID 22288810, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Amino-5-fluorophenyl)-3-(2,6-dichlorophenyl)-thiourea was dissolved in ethanol and treated with 8 equivalents of methyl iodide. The mixture was heated to reflux for 6 h. The solvent was distilled off, the residue was treated with water, then the mixture was rendered weakly alkaline by addition of saturated aqueous sodium hydrogencarbonate solution, and extracted. After distilling off the solvent, the residue was purified by column chromatography on silica gel using a mixture of methylene chloride and methanol (10:1). After distilling off the solvent under reduced pressure, the residue was dissolved using EA, and the solution was treated with excess ethereal hydrochloric acid. The mixture was stirred at RT for approximately 30 minutes, and the crystalline substance was filtered off and recrystallized from a mixture of EA and ethanol. Colorless crystalline product, m.p.: 294-296° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. distillationThe solvent was distilled off
  4. additionthe residue was treated with water
  5. additionby addition of saturated aqueous sodium hydrogencarbonate solution
  6. extractionextracted
  7. distillationAfter distilling off the solvent
  8. customthe residue was purified by column chromatography on silica gel using
  9. additiona mixture of methylene chloride and methanol (10:1)
  10. distillationAfter distilling off the solvent under reduced pressure
  11. dissolutionthe residue was dissolved
  12. additionthe solution was treated with excess ethereal hydrochloric acid
  13. filtrationthe crystalline substance was filtered off
  14. customrecrystallized from a mixture of EA and ethanol

Sources & evidence

ORD record
ord-20e4325d55eb44f8b9c7acc8ae1eb5be
Source dataset
uspto-grants-2005_10
Patent number
US06958357B2

Reaction notes

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