Thiophenol → HCID 178420562, compound

HRID 1885811Notes

Reaction equation

HRID 1885811 reaction equation
N[C:2]1[N:6]=[CH:5][NH:4][N:3]=1.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O>[C:16]1([S:22][C:2]2[N:6]=[CH:5][NH:4][N:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178418311HCID 178418311, compound

Product 1

HCID 178420562HCID 178420562, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

3-Amino-1,2,4-triazole (12 g) is dissolved in 40% sulfuric acid (26 ml), and with temperature held at 5° C. or below, a solution consisting of sodium nitrite (11.9 g) dissolved in water (36 ml) is added dropwise. Subsequently, a saturated aqueous solution of sodium acetate is added to adjust the pH of the mixture to 4-5. The resulting solution is added over 1.5 h under cooling with ice to a solution composed of thiophenol (11.6 ml), sodium hydroxide (4.72 g) and water (30 ml). The reaction is stirred at room temperature for 0.5 h, then at 40°-50° C. for 1.5 h. After the reaction, the resulting product is extracted with ethyl acetate, washed with water, and dried with magnesium sulfate. When the solvent is distilled off, an oil remains. When this is purified by silica gel chromatography (solvent: chloroform-2% methanol), an oil is produced in an amount of 12.88 g; yield, 64.9%.

Workup

  1. customheld at 5° C. or below
  2. additionis added dropwise
  3. additionThe resulting solution is added over 1.5 h
  4. temperatureunder cooling with ice to a solution
  5. waitat 40°-50° C. for 1.5 h
  6. customAfter the reaction
  7. extractionthe resulting product is extracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried with magnesium sulfate
  10. distillationWhen the solvent is distilled off
  11. customWhen this is purified by silica gel chromatography (solvent: chloroform-2% methanol)
  12. customan oil is produced in an amount of 12.88 g
  13. customyield

Sources & evidence

ORD record
ord-2d9b3fafbf3f4426a21789d1a0886561
Source dataset
uspto-grants-1992_09
Patent number
US05147445

Reaction notes

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