N-Methylacetamide → N-(3,5-dichloro-4-chloromethyl-pyridin-2-yl)-N-methyl-acetamide

HRID 1959545Notes

Reaction equation

HRID 1959545 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][NH:8][C:9](=[O:11])[CH3:10].CC1C=CC=C(C)N=1.[Cl:20][C:21]1[CH:22]=[N+:23]([O-])[CH:24]=[C:25]([Cl:29])[C:26]=1[CH2:27][Cl:28].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:20][C:21]1[C:22]([N:8]([CH3:7])[C:9](=[O:11])[CH3:10])=[N:23][CH:24]=[C:25]([Cl:29])[C:26]=1[CH2:27][Cl:28]

Participants

7

Reactant 5

HCID 6582N-MethylacetamideHCID 79372,6-LutidineHCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 670774363,5-Dichloro-4-chloromethyl-pyridine 1-oxide

Product 1

HCID 67077481N-(3,5-dichloro-4-chloromethyl-pyridin-2-yl)-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl dichloride (45 μL, 0.47 mmol) was added dropwise to a solution of N-methylacetamide (36 μL, 0.47 mmol) and 2,6-dimethyl-pyridine (55 μL, 0.47 mmol) in anhydrous DCM (10 mL) at 0° C. After stirring for 20 min, 3,5-dichloro-4-chloromethyl-pyridine 1-oxide (10 mg, 0.047 mmol) was added to it and stirring was continued overnight at 45° C. Saturated aqueous Na2CO3 solution (20 mL) and DCM (40 mL) were added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with EA/hexane 1:3) to give the title compound. MS (m/z): 267.4 [M+H+].

Workup

  1. stirringstirring
  2. waitwas continued overnight at 45° C
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography over silica gel (elution with EA/hexane 1:3)

Sources & evidence

ORD record
ord-c15b49678dc749019c75fc1d3ac762a4
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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