Methyl iodide → HCID 22288810、化合物

HRID 968298ノート

反応式

HRID 968298 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 22288810HCID 22288810、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-20e4325d55eb44f8b9c7acc8ae1eb5be
出典データセット
uspto-grants-2005_10
特許番号
US06958357B2

反応ノート

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