4-(5-bromo-2-methylbenzyl)-5-hydroxymethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one → 4-(5-bromo-2-methylbenzyl)-5-formyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1883624Notes

Reaction equation

HRID 1883624 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:12]([CH2:13][OH:14])=[N:11][N:10]([CH3:15])[C:9]1=[O:16]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:12]([CH:13]=[O:14])=[N:11][N:10]([CH3:15])[C:9]1=[O:16]

Participants

4

Reactant 1

HCID 129937754-(5-bromo-2-methylbenzyl)-5-hydroxymethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 129940054-(5-bromo-2-methylbenzyl)-5-formyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

7.46 g (23.9 mmol) of 4-(5-bromo-2-methylbenzyl)-5-hydroxymethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 15.8 g of active manganese dioxide were stirred for 3 hours in nitrogen atmosphere under reflux with heating in 71 ml of chloroform. The reaction solution was filtrated through celite, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate-1/2 (v/v)), to obtain 5.04 g (16.3 mmol) of 4-(5-bromo-2-methylbenzyl)-5-formyl-2-methyl-2,4-dihydro-3H-1,2, 4-triazol-3-one having a melting point of 107.5° C.

Workup

  1. temperatureunder reflux
  2. filtrationThe reaction solution was filtrated through celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-59b00f8dd1f745fdada0ca80e6d5a602
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

Loading…