Methane → HCID 20232005, compound

HRID 2290364Notes

Reaction equation

HRID 2290364 reaction equation
ON=[C:3]([CH3:18])[C:4](=[N:13][NH:14][C:15]([NH2:17])=[S:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[C:19](=O)([O-])[O-].[K+].[K+].C.CI>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]2[N:13]=[N:14][C:15]([S:16][CH3:19])=[N:17][C:3]=2[CH3:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136442194HCID 136442194, compound

Product 1

HCID 20232005HCID 20232005, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-hydroxyimino-4'-methoxypropiophenone thiosemicarbazone (5.32 g), potassium carbonate (6.35 g) and water (50 ml) was treated in a similar manner to that of Example 25-(2), and then treated with activated charcoal. To the filtrate was added methyl iodide (6 g), and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, treated with silica gel, and filtered. The filtrate was concentrated to dryness to give a residue, which was crystallized from diisopropyl ether. The resultant crystals were collected by filtration, washed with diisopropyl ether and dried to give 6-(4-methoxyphenyl)-5-methyl-3-methylthio-1,2,4,-triazine (2.42 g).

Workup

  1. additionwas treated in a similar manner to that of Example 25-(2)
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. additiontreated with silica gel
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness
  8. customto give a residue, which
  9. customwas crystallized from diisopropyl ether
  10. filtrationThe resultant crystals were collected by filtration
  11. washwashed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-b8d19417b5754c5aa89743b25ab0b531
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

Loading…