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Sodium Hydroxide → N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

HRID 1894646
ノート
印刷プレビュー

反応式

HRID 1894646 の反応式
[CH2:1]([N:3]([CH3:6])[CH:4]=O)[CH3:2].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[CH3:20])=[CH:10][C:9]=1[C:23]([F:26])([F:25])[F:24].[OH-].[Na+]>ClCCl>[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[N:18]=[CH:17][C:16]([N:19]=[CH:4][N:3]([CH2:1][CH3:2])[CH3:6])=[CH:15][C:14]=2[CH3:20])=[CH:10][C:9]=1[C:23]([F:26])([F:24])[F:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 350667N-ethyl-N-methylformamideHCID 581533506-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine

生成物 1

HCID 25158782N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine収率 70.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

In a 25 ml single-necked round-bottomed flask, ethylmethylformamide (350 mg) is solubilized in dry dichloromethane (4 ml) at ambient temperature (colourless solution). Under stirring phosphorous oxide chloride (0.4 ml) is added dropwise by syringe. Stirring at ambient temperature is continued for 1 hour, whereupon a pink-orange solution is obtained. To this solution, 6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.6 g) dissolved in 1.0 ml of dry dichloromethane is added dropwise by syringe, giving a yellow solution. Stirring is continued at an ambient temperature for 1 hour. The mixture is then poured into ice/water (pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about 11 and stirring is continued for 10 minutes. The mixture is then extracted with dichloromethane (2×50 ml). The combined organic phases are then dried over sodium sulfate, filtered and the solvent is removed in vacuo. Purification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 1:2 (v:v) gives 0.52 g of the compound as a yellow oil.

後処理

  1. additionUnder stirring phosphorous oxide chloride (0.4 ml) is added dropwise by syringe
  2. customis obtained
  3. additionis added dropwise by syringe
  4. customgiving a yellow solution
  5. stirringStirring
  6. waitis continued at an ambient temperature for 1 hour
  7. customto get a pH of about 11
  8. stirringstirring
  9. waitis continued for 10 minutes
  10. extractionThe mixture is then extracted with dichloromethane (2×50 ml)
  11. dry with materialThe combined organic phases are then dried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent is removed in vacuo
  14. customPurification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 1:2 (v:v)

出典と根拠

ORDレコード
ord-a898716a009042cb872c095c51bae21e
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08513286B2

反応ノート

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