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

HRID 2245936Notes

Reaction equation

HRID 2245936 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[C:6]([C:14]([OH:16])=O)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+].[CH3:19]I>O.CO>[CH3:19][S:4][C:3]1[NH:5][C:14](=[O:16])[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:1][N:2]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11915Phenylglyoxylic AcidHCID 14797Potassium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 1354506073-(Methylsulfanyl)-6-phenyl-1,2,4-triazin-5(2H)-oneYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of thiosemicarbazide (1.8 g, 0.020 mol) and benzoylformic acid (3.0 g, 0.020 mol) in water (50 mL) was heated under reflux for 15 min. Then potassium hydroxide (1.5 g, 0.027 mol) in methanol (50 mL) was added at 80° C. The reaction mixture was stirred and heated at 80° C. for 2 days. After cooling to 35° C., methyl iodide (1.4 mL, 0.022 mol) was added. The reaction mixture was stirred at 40° C. for 30 min. The mixture was concentrated. The precipitate formed was collected by filtration, washed with water, and dried under vacuum to afford the desired product (4.3 g, 97.7%). Analytical LCMS: (M+H)+=220.1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 min
  3. temperatureAfter cooling to 35° C.
  4. stirringThe reaction mixture was stirred at 40° C. for 30 min
  5. concentrationThe mixture was concentrated
  6. customThe precipitate formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-4564dfeef2094d5993d4391aaa6de910
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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