Bromomethyl 4-methoxyphenyl ketone → 3-(p-Methoxy-phenacylmercapto)-4-n-butyl-1,2,4-triazole

HRID 1112110Notes

Reaction equation

HRID 1112110 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+].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:16]>CO>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][S:1][C:2]2[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][N:3]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 14798Sodium HydroxideHCID 178448642HCID 178448642, compound

Product 1

HCID 128884643-(p-Methoxy-phenacylmercapto)-4-n-butyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-mercapto-4-n-butyl-1,2,4-triazole (10 g. or 0.063 mole) and sodium hydroxide (2.55 g. or 0.0637 mole) in 200 ml. of methanol was added α-bromo-p-methoxyacetophenone (15.3 g. or 0.067 mole). The reaction mixture was heated at reflux for 16 hours and the solvent removed in vacuum to leave a solid residue. The solid was washed with water and recrystallized from benzene-hexane to give 3-(p-methoxy-phenacylmercapto)-4-n-butyl-1,2,4-triazole melting at 79°-82° C. The structure was confirmed by its infrared and nuclear magnetic spectra.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. customthe solvent removed in vacuum
  4. customto leave a solid residue
  5. washThe solid was washed with water
  6. customrecrystallized from benzene-hexane

Sources & evidence

ORD record
ord-e9809cf5a2f34f45aba3e25b02b33eb1
Source dataset
uspto-grants-1978_10
Patent number
US04120864

Reaction notes

Loading…