Calcium Chloride → 5-amino-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine

HRID 856624Notes

Reaction equation

HRID 856624 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[N:16]([CH2:17][CH2:18][CH3:19])[CH:15]=[N:14][N:13]=2)=[N:8][CH:9]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[N:16]([CH2:17][CH2:18][CH3:19])[CH:15]=[N:14][N:13]=2)=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 22938905HCID 22938905, compound

Product 1

HCID 229384395-amino-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridineYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-nitro-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine (4.0 g), reduced iron (4.0 g), and calcium chloride (0.79 g) was added to 85% aqueous solution of ethanol (100 ml), and the mixture was refluxed for 3 hours. The reaction solution was filtered with Celite, and the solvent of the filtrate was distilled off. The residue was purified by basic silica gel column chromatography (elution solvent: methanol/ethyl acetate), to give 5-amino-2-(4-propyl-4H-1,2,4-triazol-3-yl)methylthiopyridine (3.3 g) as red oil.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationThe reaction solution was filtered with Celite
  3. distillationthe solvent of the filtrate was distilled off
  4. customThe residue was purified by basic silica gel column chromatography (elution solvent: methanol/ethyl acetate)

Sources & evidence

ORD record
ord-9b7cc4b967784759878886b465b29da4
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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