Dimethyl Sulfoxide → n-Pyridin-2-yl-n-(pyridin-2-ylmethyl)pyridin-2-amine

HRID 1471279

Reaction equation

HRID 1471279 reaction equation
[OH-].[K+].CS(C)=O.[CH:7]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=[CH:9][CH:8]=1.Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>O>[N:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:13]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:11]1[CH:12]=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 145472,2'-DipyridylamineHCID 14797Potassium HydroxideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 15554506n-Pyridin-2-yl-n-(pyridin-2-ylmethyl)pyridin-2-amineYield 55.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 5.2 g pulverized potassium hydroxide and 35 ml dimethylsulfoxide. After adding 3.4 g 2,2′-dipyridylamine, the mixture was stirred under nitrogen for 45 minutes, when 3.3 g 2-(chloromethyl)pyridine hydrochloride was added. After stirring for 1 hour, 100 ml of water was added and the product was extracted with 60 ml of 50% ethyl acetate, 50% hexane. The organic layer was washed with 30 ml water and the solvent was removed. The residue was added to 5 ml hot ethanol, and 20 ml of water was added. After cooling to 5 C, the solid was filtered and washed with water. The product was dissolved in 20 ml hot ethanol and treated with 150 mg activated carbon. After hot filtration through celite, 40 ml of water were added and the mixture was cooled to 5 C. The product was filtered, washed with 20 ml 20% ethanol in water, and dried resulting in 2.9 g of an off-white solid.

Workup

  1. additionTo a flask were added 5.2 g
  2. stirringAfter stirring for 1 hour
  3. extractionthe product was extracted with 60 ml of 50% ethyl acetate, 50% hexane
  4. washThe organic layer was washed with 30 ml water
  5. customthe solvent was removed
  6. additionThe residue was added to 5 ml hot ethanol, and 20 ml of water
  7. additionwas added
  8. temperatureAfter cooling to 5 C
  9. filtrationthe solid was filtered
  10. washwashed with water
  11. dissolutionThe product was dissolved in 20 ml hot ethanol
  12. additiontreated with 150 mg
  13. filtrationAfter hot filtration through celite, 40 ml of water
  14. additionwere added
  15. temperaturethe mixture was cooled to 5 C
  16. filtrationThe product was filtered
  17. washwashed with 20 ml 20% ethanol in water
  18. customdried

Sources & evidence

ORD record
ord-a0c6e64f50eb495998d24fe38dae50cc
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Linked notes

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