Methyl iodide → 6-(4-Fluorophenyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one

HRID 607557Notes

Reaction equation

HRID 607557 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([O:11]C)=O)=[CH:4][CH:3]=1.[NH2:14][NH:15][C:16]([NH2:18])=[S:17].[OH-].[K+].[CH3:21]I>O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:11])[NH:18][C:16]([S:17][CH3:21])=[N:15][N:14]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 2723789ThiosemicarbazideHCID 10965144Methyl 2-(4-fluorophenyl)-2-oxoacetate

Product 1

HCID 1356045966-(4-Fluorophenyl)-3-(methylthio)-1,2,4-triazin-5(4H)-oneYield 85.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl (4-fluorophenyl)(oxo)acetate (1.1 g, 0.0059 mol), thiosemicarbazide (0.54 g, 0.0059 mol) in water (10 mL) was heated at reflux for 15 min. Then methanol (10 mL) was added, followed by potassium hydroxide (0.43 g, 0.0077 mol). The mixture was stirred at 90° C. overnight. After cooling, methyl iodide (4 mL, 0.06 mol) was added. The mixture was stirred at RT for 30 min. The precipitate formed was collected by filtration, washed with ether, and dried under high vacuum to give the desired product (1.2 g, 77%). Analytical LCMS: (M+H)+=238.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. temperatureAfter cooling
  4. stirringThe mixture was stirred at RT for 30 min
  5. customThe precipitate formed
  6. filtrationwas collected by filtration
  7. washwashed with ether
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-d898496c45fe4d0ca21558f9be65164c
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

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