Diethylamine → HCID 86038276, compound

HRID 2245549Notes

Reaction equation

HRID 2245549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N+:3]=1[O-:10].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N+:3]([O-:10])=[CH:4][C:5]([CH2:8][N:13]([CH2:14][CH3:15])[CH2:11][CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 86038276HCID 86038276, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-5-chloromethylpyridine 1-oxide (1.78 g, 10.0 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333), diethyl amine (1.46 g, 20.0 mmol), and potassium carbonate (1.38 g, 10.0 mmol) were mixed in acetonitrile (50 mL) at room temperature. The mixture was stirred for 16 h, the solvent was removed in vacuo, and the residue was purified on a silica gel column using chloroform/methanol, (9:1), as the eluent to give 1.90 g (88% yield) of the title compound as a pale orange oil: MS (EI) m/z 215 and 217 (M++1).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-94df0d1d15dc4852a2486206f7bfe945
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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