Benzylamine → HCID 15896238, compound

HRID 1274900Notes

Reaction equation

HRID 1274900 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=O)[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:13][N:14]=1.S(Cl)(Cl)=O.O1CCCC1.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[CH2:31]([NH:38][C:10]1[N:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:13]=[N:14][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 135618710HCID 135618710, compound

Product 1

HCID 15896238HCID 15896238, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(2,4-dichlorophenyl)-3-(2-pyridyl)-1,2,4-triazin-5-one (5.00 g, 15.7 mmol) and thionyl chloride (50 ml) was heated under reflux for two hours. The mixture was allowed to cool to room temperature, and the solvent was removed by distillation under reduced pressure. To the residue were added tetrahydrofuran (50 ml), benzylamine (4.20 g, 39.2 mmol, 2.5 eq.), and the mixture was heated under reflux for two hours. The mixture was allowed to cool to room temperature, and water (150 ml) was added to the reaction mixture. The mixture was extracted with methylene chloride (600 ml), and washed with a 5% aqueous potassium hydrogen carbonate solution (150 ml), and further washed with a 5% brine (150 ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was purified by flash silica gel column chromatography (methylene chloride) to give the title compound as pale yellow crystals (3.64 g, 57%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. customthe solvent was removed by distillation under reduced pressure
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for two hours
  6. temperatureto cool to room temperature
  7. extractionThe mixture was extracted with methylene chloride (600 ml)
  8. washwashed with a 5% aqueous potassium hydrogen carbonate solution (150 ml)
  9. washfurther washed with a 5% brine (150 ml)
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting solid was purified by flash silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-3ab3ceb36cc8494f86a0f84f8a11a854
Source dataset
uspto-grants-2000_12
Patent number
US06159974

Reaction notes

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