HCID 22008532, compound → 2-(3,5-Dichloro-4-(4-chlorobenzyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1604322Notes

Reaction equation

HRID 1604322 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[C:12]([Cl:13])=[CH:11][C:10]([N:14]3[C:19](=[O:20])[NH:18][CH2:17][CH:16]=[N:15]3)=[CH:9][C:8]=2[Cl:21])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[C:12]([Cl:13])=[CH:11][C:10]([N:14]3[C:19](=[O:20])[NH:18][C:17](=[O:25])[CH:16]=[N:15]3)=[CH:9][C:8]=2[Cl:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22008532HCID 22008532, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 150529132-(3,5-Dichloro-4-(4-chlorobenzyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dioneYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran was dissolved 2.6 g of 2-[4-(4-chlorobenzyl)-3,5-dichlorophenyl]-4,5-dihydro-1,2,4-triazin-3(2H)-one. To the solution was added 4.5 g of pyridinium chlorochromate. The mixture was stirred at room temperature overnight, after which the insoluble matter was filtered off. The filtrate was concentrated. The residue was purified by column chromatography (Merck Silica Gel 60; chloroform-ethanol=20:1) to provide 2.2 g of the title compound as colorless crystals, m.p. 175-176° C.

Workup

  1. filtrationafter which the insoluble matter was filtered off
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by column chromatography (Merck Silica Gel 60; chloroform-ethanol=20:1)

Sources & evidence

ORD record
ord-59130b63a51944e38ee48a9f7d48ee33
Source dataset
uspto-grants-1999_11
Patent number
US05994355

Reaction notes

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