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

HRID 477732Notes

Reaction equation

HRID 477732 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([SH:7])[NH:4][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:3][N:4]=[C:5]([S:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 1785092965-amino-1H-1,2,4-triazole-3-thiol

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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

Workup

  1. additionwas added
  2. filtrationwas then filtered
  3. customThe ethanol was evaporated off
  4. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b82cfc36a6374223bdd0d890c06b2c86
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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