Acetic Anhydride → N-(5,6-Dichloro-pyridin-3-ylmethyl)-acetamide

HRID 730869Notes

Reaction equation

HRID 730869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10]C)[CH:5]=[N:6][C:7]=1[Cl:8].CCN(CC)CC.CC(O[C:23]([CH3:25])=[O:24])=O>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:23](=[O:24])[CH3:25])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 85663685[(5,6-Dichloropyridin-3-yl)methyl](methyl)amine

Product 1

HCID 19959722N-(5,6-Dichloro-pyridin-3-ylmethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the amine from step (c) above (1.77 g, 10 mmol) and Et3N (2.78 mL, 20 mmol, Aldrich) was added Ac2O dropwise with stirring at room temperature. The mixture was stirred for 30 min at room temperature, diluted with EtOAc (30 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 80% EtOAc/hexane to give the title compound. MS (ESI, pos. ion) m/z: 219 (M+1).

Workup

  1. stirringThe mixture was stirred for 30 min at room temperature
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with 80% EtOAc/hexane

Sources & evidence

ORD record
ord-a51c7a5d6cec4a5fb3759e567f2db6ed
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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