Water → HCID 178510105, compound

HRID 1289783Notes

Reaction equation

HRID 1289783 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]=[C:7]([SH:9])[NH:6][N:5]=1.Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.O>CN(C)C=O>[NH2:3][C:4]1[N:8]=[C:7]([S:9][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[NH:6][N:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 121634-ChlorobenzonitrileHCID 24758Sodium hydrideHCID 1785092965-amino-1H-1,2,4-triazole-3-thiol

Product 1

HCID 178510105HCID 178510105, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 60% sodium hydride-in-oil (3.89 g) in dimethylformamide (50 ml) was dropwise added a solution (100 ml) of 3-amino-5-mercapto-1H-1,2,4-triazole (10.0 g) in dimethylformamide under ice-cooling. After the dropwise addition, the mixture was stirred at 0° C.-room temperature for 30 minutes and ice-cooled again. A solution (50 ml) of 4-chlorobenzonitrile (13.0 g) in dimethylformamide was dropwise added. The mixture was stirred at 0° C.-room temperature for 30 minutes and at 100°-110° C. for 33 hours. After the reaction, the mixture was cooled to room temperature and added with water, followed by stirring for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The crude product was subjected to silica gel column chromatography (chloroform-methanol) to give 1.86 g of white crystals (yield 9.9%).

Workup

  1. temperaturecooling
  2. additionAfter the dropwise addition
  3. temperatureice-cooled again
  4. stirringThe mixture was stirred at 0° C.-room temperature for 30 minutes and at 100°-110° C. for 33 hours
  5. customAfter the reaction
  6. stirringby stirring for 30 minutes
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-ba75ff8b0f4a4ac4973a9427378444d3
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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