Potassium Carbonate → 2,3,4-Trichloro-6-(5-oxazolyl)pyridine

HRID 1837443Notes

Reaction equation

HRID 1837443 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH:10]=[O:11])[CH:3]=1.S([CH2:22][N+:23]#[C-:24])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:9][C:6]1[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=[C:4]([C:10]2[O:11][CH:24]=[N:23][CH:22]=2)[N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 129936954,5,6-Trichloropyridine-2-carbaldehyde

Product 1

HCID 129936962,3,4-Trichloro-6-(5-oxazolyl)pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4,5,6-trichloropyridine-2-carbaldehyde (1.66 g, 8 mmol), tosylmethyl isocyanide (1.54 g, 8 mmol) and potassium carbonate (1.09 g, 8 mmol) in methanol (20 mL) was heated at 50° C. for 30 min and then heated at 80° C. for 5 min. The solvent was removed by rotary evaporation and the residue was suspended in water (200 mL) and stirred vigorously. The precipitate was collected by suction filtration, washed with water and air-dried to provide of 2,3,4-trichloro-6-(5-oxazolyl)pyridine (1.7 g, 6.8 mmol), mp 128-130° C.

Workup

  1. temperatureheated at 80° C. for 5 min
  2. customThe solvent was removed by rotary evaporation
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-b7435f37d7b641d387a59032df4e7840
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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