Sodium Hydroxide → 3-(4-Methoxybenzylmercapto)-4-n-butyl-1,2,4-triazole

HRID 1680094Notes

Reaction equation

HRID 1680094 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][N:3]=1.[OH-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CO>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][S:1][C:2]2[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 178448642HCID 178448642, compound

Product 1

HCID 128884523-(4-Methoxybenzylmercapto)-4-n-butyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 10 g. (0.064 mole) of 3-mercapto-4-n-butyl-1,2,4-triazole and 2.6 g. (0.064 mole) of sodium hydroxide in 200 ml. of methanol was added 9.9 g. (0.064 mole) of p-methoxybenzyl chloride. The reaction mixture was heated at reflux about 20 hours. The solvent was evaporated off, the residue washed with water, dried and distilled. There was obtained 17.8 g. of yellow liquid distilling at 190°-205° C. at 0.03 mm. Nuclear magnetic resonance and ultraviolet spectra indicated this to be approximately an equal mixture of 3-(4-methoxybenzylmercapto)-4-n-butyl-1,2,4-triazole and 4-n-butyl-2-(4-methoxybenzyl)-1,2,4-triazoline-3-thione.

Workup

  1. additionTo a mixture of 10 g
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux about 20 hours
  4. customThe solvent was evaporated off
  5. washthe residue washed with water
  6. customdried
  7. distillationdistilled
  8. customThere was obtained 17.8 g
  9. distillationof yellow liquid distilling at 190°-205° C. at 0.03 mm
  10. additionan equal mixture of 3-(4-methoxybenzylmercapto)-4-n-butyl-1,2,4-triazole and 4-n-butyl-2-(4-methoxybenzyl)-1,2,4-triazoline-3-thione

Sources & evidence

ORD record
ord-7dbfb0106398413b885a34c590ee5267
Source dataset
uspto-grants-1981_06
Patent number
US04271308

Reaction notes

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