Methane → HCID 15592370, compound

HRID 2418124Notes

Reaction equation

HRID 2418124 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].[OH-].[Na+].C.[H][H]>C(Cl)Cl.C(OCC)(=O)C>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1)=[O:19]

Participants

9

Reactant 6

HCID 297MethaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 793055-Amino-2-chloropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 15592370HCID 15592370, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled solution of 45 g (0.35 mole) of 5-amino-2-chloropyridine and 42.4 g (0.42 mole) of triethylamine in 300 ml of CH2Cl2 was added, dropwise, a solution of 44.3 g (0.368 moles) of trimethyl acetyl chloride in 60 ml of dichloromethane over a period of 1.5 hours. This mixture was stirred at room temperature for 2 hours, poured into 5% aqueous NaOH and the dichloromethane layer separated. The organic layer was washed with 5% aqueous NaOH, dried over Na2SO4 and evaporated to leave a brown oil which solidified on standing. This solid was taken up in hot ethyl acetate, treated with charcoal, filtered and diluted with hexane. Cooling this solution resulted in the precipitation of 58.7 g (79% of theoretical) of white crystals having a melting point of 120°-123° C. Carbon, hydrogen and nitrogen content calculated for C10H13ClN2O is C, 56.47; H, 6.16; and N, 13.17 percent by weight which compared to that actually found of C, 56.31; H, 6.14; and N, 13.02 percent by weight.

Workup

  1. additionwas added
  2. customthe dichloromethane layer separated
  3. washThe organic layer was washed with 5% aqueous NaOH
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto leave a brown oil which
  7. filtrationfiltered
  8. additiondiluted with hexane
  9. temperatureCooling this solution
  10. customresulted in the precipitation of 58.7 g (79% of theoretical) of white crystals

Sources & evidence

ORD record
ord-ec83f63e3bfd4d189e18bfdb6547d2c9
Source dataset
uspto-grants-1984_09
Patent number
US04472193

Reaction notes

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