Dichloromethane → N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-pyridin-2-yl-formamidine

HRID 1894647노트

반응식

HRID 1894647 반응식
[CH3:1][N:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH:3]=O.[Cl:11][C:12]1[CH:26]=[CH:25][C:15]([O:16][C:17]2[N:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=2[CH3:24])=[CH:14][C:13]=1[C:27]([F:30])([F:29])[F:28].[OH-].[Na+].Cl[CH2:34]Cl>>[Cl:11][C:12]1[CH:26]=[CH:25][C:15]([O:16][C:17]2[N:22]=[CH:21][C:20]([N:23]=[CH:1][N:2]([CH2:3][CH3:34])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)=[CH:19][C:18]=2[CH3:24])=[CH:14][C:13]=1[C:27]([F:30])([F:28])[F:29]

참가 물질

5

반응물 4

HCID 6344Dichloromethane2회HCID 14798Sodium HydroxideHCID 572611N-Methyl-N-(pyridine-2-yl)formamideHCID 581533506-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine

생성물 1

HCID 66940279N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-pyridin-2-yl-formamidine

실험 절차

In a 25 ml single-necked round-bottomed flask, N-methyl-N-pyridin-2-yl-formamide (0.5 ml) 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-(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 1:1 (v:v) gives 0.33 g of the compound as a yellow oil.

후처리

  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 of this gum by flash chromatography over silica gel with hexane/ethyl acetate 1:1 (v:v)

출처 및 근거

ORD 기록
ord-78f0ca74cc744096926d7f1251b7daa0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513286B2

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