Sodium Hydroxide → N'-[6-(2,4-Dichloro-phenoxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

HRID 508476ノート

反応式

HRID 508476 の反応式
[CH2:1]([N:3]([CH3:6])[CH:4]=O)[CH3:2].[Cl:7][C:8]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.[OH-].[Na+]>ClCCl>[Cl:7][C:8]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[N:16]=[CH:15][C:14]([N:17]=[CH:4][N:3]([CH2:1][CH3:2])[CH3:6])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 350667N-ethyl-N-methylformamideHCID 7357766-(2,4-Dichlorophenoxy)pyridin-3-amine

生成物 1

HCID 25158514N'-[6-(2,4-Dichloro-phenoxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidine収率 48.8%

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. To this solution, 6-(2,4-Dichloro-phenoxy)-pyridin-3-ylamine (0.5 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 by flash chromatography over silica gel with hexane/ethyl acetate 3:4 (v:v) gives 0.31 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. additionis added dropwise by syringe
  3. customgiving a yellow solution
  4. stirringStirring
  5. waitis continued at an ambient temperature for 1 hour
  6. customto get a pH of about 11
  7. stirringstirring
  8. waitis continued for 10 minutes
  9. extractionThe mixture is then extracted with dichloromethane (2×50 ml)
  10. dry with materialThe combined organic phases are then dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent is removed in vacuo
  13. customPurification by flash chromatography over silica gel with hexane/ethyl acetate 3:4 (v:v)

出典と根拠

ORDレコード
ord-b4aba6412d5443dabfb7da7349f02e8a
出典データセット
uspto-grants-2015_08
特許番号
US09096525B2

反応ノート

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