Methane → HCID 20232094, compound

HRID 2290360Notes

Reaction equation

HRID 2290360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:13][NH:14][C:15]([NH2:17])=[S:16])[C:9](=NO)[CH3:10])=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[N:14][C:15]([S:16][CH3:18])=[N:17][C:9]=2[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 11430Potassium CarbonateHCID 136332165HCID 136332165, compound

Product 1

HCID 20232094HCID 20232094, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4'-chloro-2-hydroxyiminopropiophenone thiosemicarbazone (113.21 g), potassium carbonate (128.71 g) and water (990 ml) was refluxed for 25 hours with stirring, and the reaction mixture was treated with activated charcoal and filtered by suction. To the filtrate was added dropwise methyl iodide (76 g) with stirring, and the stirring was continued for 15 minutes at room temperature. The resulting solid was collected by filtration, washed with water and dissolved in chloroform. The solution was treated with silica gel and filtered, and the filtrate was evaporated under reduced pressure. The residue was washed with diisopropyl ether and dried to give a solid of 6-(4-chlorophenyl)-5-methyl-3-methylthio-1,2,4-triazine (61.1 g).

Workup

  1. temperaturewas refluxed for 25 hours
  2. filtrationfiltered by suction
  3. additionTo the filtrate was added dropwise methyl iodide (76 g)
  4. stirringwith stirring
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in chloroform
  8. additionThe solution was treated with silica gel
  9. filtrationfiltered
  10. customthe filtrate was evaporated under reduced pressure
  11. washThe residue was washed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-44c74fc1e3dd4da9b4bab78e05011164
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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