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

HRID 508476Notes

Reaction equation

HRID 508476 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b4aba6412d5443dabfb7da7349f02e8a
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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