Potassium Carbonate → HCID 22938905, compound

HRID 856623Notes

Reaction equation

HRID 856623 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.Cl[CH2:13][C:14]1[N:18]([CH2:19][CH2:20][CH3:21])[CH:17]=[N:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH3:21])[CH:17]=[N:16][N:15]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 229387553-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochlorideHCID 178526723C5H4N2O2S

Product 1

HCID 22938905HCID 22938905, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-mercapto-5-nitropyridine (5.0 g), 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride (6.3 g) and potassium carbonate (11 g) was added to N,N-dimethylformamide (100 ml), and the mixture was stirred overnight at room temperature. The solvent was distilled off, and to the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give 5-nitro-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine (8.0 g) as brown crystals.

Workup

  1. distillationThe solvent was distilled off
  2. additionto the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-80afcae74f2b4c1390683f6cd8ee6c51
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…