Thiophenol → HCID 53663221, compound

HRID 2290743Notes

Reaction equation

HRID 2290743 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>O>[C:16]1([S:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 53663221HCID 53663221, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Using 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1 g) in a similar manner to that of Example 18-(1), a diazonium salt-containing aqueous solution was produced. With stirring at 80° C., this solution was added dropwise to a solution composed of thiophenol (1.04 g), sodium hydroxide (0.45 g) and water (5 ml) and the mixture was refluxed for further 15 minutes. After cooling, the precipitate was recovered by filtration and dissolved in a mixture of chloroform and methanol. The solution was washed with aqueous sodium hydroxide and water in that order and concentrated to dryness under reduced pressure. The residue was purified by silica gel (30 g) column chromatography (eluent: ethyl acetate) to give 6-(4-phenylthiophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.46 g).

Workup

  1. customwas produced
  2. additionthis solution was added dropwise to a solution
  3. temperaturethe mixture was refluxed for further 15 minutes
  4. temperatureAfter cooling
  5. filtrationthe precipitate was recovered by filtration
  6. dissolutiondissolved in a mixture of chloroform and methanol
  7. washThe solution was washed with aqueous sodium hydroxide and water in that order
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was purified by silica gel (30 g) column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-cc72202817274fcbacd9f5329d8bdf2f
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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