Methyl iodide → Metribuzin

HRID 1105655Notes

Reaction equation

HRID 1105655 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:5][N:4]=[C:3]1[SH:13].[OH-].[Na+].[CH3:16]I>O>[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]([CH3:10])([CH3:12])[CH3:11])=[N:5][N:4]=[C:3]1[S:13][CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178441961HCID 178441961, compound

Product 1

HCID 30479MetribuzinYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

168.6 g (0.84 mol) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one were introduced into a mixture of 820 g of 45% strength sodium hydroxide solution and 550 g of water, while stirring. When the product had dissolved completely, 140 g of methyl iodide were added in a manner such that the internal temperature did not exceed 30° C. When the addition had ended, the reaction solution was stirred for a further two hours at room temperature. Thereafter, the solid formed was filtered off, washed with 1,000 ml of water and dried at 60° C. in a vacuum drying cabinet. 146 g (81% of theory) of 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5(4H)-one (VIII) of melting point 123°-125° C. were obtained.

Workup

  1. dissolutionWhen the product had dissolved completely
  2. customdid not exceed 30° C
  3. additionWhen the addition
  4. stirringthe reaction solution was stirred for a further two hours at room temperature
  5. customThereafter, the solid formed
  6. filtrationwas filtered off
  7. washwashed with 1,000 ml of water
  8. customdried at 60° C. in a vacuum
  9. customdrying cabinet

Sources & evidence

ORD record
ord-7779a5c9163e4d42b69502c8f5ec8b1b
Source dataset
uspto-grants-1982_01
Patent number
US04309538

Reaction notes

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