Sodium Hydroxide → N'-[6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

HRID 508474Notes

Reaction equation

HRID 508474 reaction equation
[CH2:1]([N:3]([CH3:6])[CH:4]=O)[CH3:2].[C:7]([C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=1)[O:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[CH3:22])([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+]>ClCCl>[C:7]([C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=1)[O:14][C:15]1[N:20]=[CH:19][C:18]([N:21]=[CH:4][N:3]([CH2:1][CH3:2])[CH3:6])=[CH:17][C:16]=1[CH3:22])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 350667N-ethyl-N-methylformamideHCID 550806946-(3-Tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine

Product 1

HCID 25158780N'-[6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidineYield 86.5%

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 0.5 hour, whereupon a pink-orange solution is obtained. To this solution, 6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.51 g) dissolved in 5.0 ml of dry dichloromethane is added dropwise by syringe, giving a yellow solution. Stirring is continued at an ambient temperature for 2 hours. 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 ethyl acetate gives 0.56 g of the compound as a brown oil.

Workup

  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 2 hours
  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 ethyl acetate

Sources & evidence

ORD record
ord-8161fc170af84687963f5f496ded4ca9
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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