Methyl Bromide → 6-tert-Butyl-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

HRID 543564Notes

Reaction equation

HRID 543564 reaction equation
[C:1]([CH:5]1[NH:10][NH:9][C:8](=[S:11])[N:7]([CH3:12])[C:6]1=[O:13])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:16]I.CBr>O>[C:1]([C:5]1[C:6](=[O:13])[N:7]([CH3:12])[C:8]([S:11][CH3:16])=[N:9][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6323Methyl BromideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13377186HCID 13377186, compound

Product 1

HCID 64543296-tert-Butyl-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 ml of 3-benzyl-4-hydroxy-biphenyl polyglycol ether, as an emulsifier, and 5,690 g (28.6 mol) of 6-tert.-butyl-4-methyl-5-oxo-3-thioxo-tetrahydro-1,2,4-(2H,4H)-triazine were added to a solution of 1,145 g of NaOH in 57 liters of water. 4,302 g (30.3 mol) of methyl iodide were added dropwise (or 2,900 g of methyl bromide were passed in) and the mixture was subsequently stirred until the slightly exothermic reaction had ended and the pH value had reached 7-8. After filtering off the product, washing it with water and drying it at 50° C., 5,810 g (95% of theory) of the compound (IIa) of melting point 90°-100° C. were obtained. The crude product was sufficiently pure for further reaction. A sample recrystallised from methanol or petroleum ether melted at 104°-105° C.

Workup

  1. filtrationAfter filtering off the product
  2. washwashing it with water
  3. customdrying it at 50° C.
  4. custom5,810 g (95% of theory) of the compound (IIa) of melting point 90°-100° C. were obtained
  5. customA sample recrystallised from methanol or petroleum ether melted at 104°-105° C.

Sources & evidence

ORD record
ord-98e954d16fa04f79989f5bceb1abc497
Source dataset
uspto-grants-1984_05
Patent number
US04447258

Reaction notes

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