Benzyl Chloride → 5-(benzylsulfanyl)-4H-1,2,4-triazol-3-amine

HRID 477739Notes

Reaction equation

HRID 477739 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([SH:7])[N:3]=1.[OH-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 178509066HCID 178509066, compound

Product 1

HCID 7372725-(benzylsulfanyl)-4H-1,2,4-triazol-3-amineYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-3-mercapto-1,2,4-triazole (40.36 g) in ethanol (450 ml) was treated at room temperature with solid sodium hydroxide (13.9 g), and benzyl chloride (44.3 g) was added dropwise. The solution was stirred overnight, filtered, and the residue was recrystallised from ethyl acetate and dried to give 64.97 g of desired product, mp 104° C.

Workup

  1. additionwas added dropwise
  2. filtrationfiltered
  3. customthe residue was recrystallised from ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-6fd3a55b65164c879b0f4f5236978b3e
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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