Potassium Carbonate → 2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

HRID 1050678Notes

Reaction equation

HRID 1050678 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][NH+:6]=[CH:5][CH:4]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:6]1[CH:7]=[CH:8][C:3]([N:10]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]3=[N:9]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 221178644-Chloropyridinium hydrochlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 64134402-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloropyridinium hydrochloride (25.0 g, 166 mmol), benzotriazole (29.6 g, 249 mmol), potassium carbonate (69.1 g, 500 mmol), and dimethylformamide (500 mL) was stirred and heated under argon at 130° C. for 3 days. After cooling, the solid was filtered off, and the solvent was evaporated under reduced pressure. The residue was treated with dichloromethane (200 mL), filtered and chromatographed using a column filled with silica gel (500 mL) and hexane/ethyl acetate (1:1) as an eluent. Fractions containing the desired product were combined, and the solvent was distilled off. The residue was triturated with ethanol, the solid was filtered off and dried in a vacuum oven to give 2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole, 6.45 (20%). 1H NMR (400 MHz, CDCl3): δ 8.80 (m, 2H, pyridine), 8.26 (m, 2H, pyridine), 7.93 (m, 2H, benzotriazole), 7.46 (m, 2H, benzotriazole).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was treated with dichloromethane (200 mL)
  5. filtrationfiltered
  6. customchromatographed
  7. additionfilled with silica gel (500 mL) and hexane/ethyl acetate (1:1) as an eluent
  8. additionFractions containing the desired product
  9. distillationthe solvent was distilled off
  10. customThe residue was triturated with ethanol
  11. filtrationthe solid was filtered off
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d8359b693638415aab998381cbfded6d
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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