Methyl iodide → Metribuzin

HRID 1065104

Reaction equation

HRID 1065104 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 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48.6 g (0.243 mol) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (V) were introduced into a mixture of 236 g of 45% strength sodium hydroxide solution and 160 g of water, while stirring. When all of the product had dissolved, 40.2 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 mixture was stirred at room temperature for a further 2 hours. The reaction product which had precipitated was then filtered off, washed with 100 ml of water and dried. 42.5 g (82% of theory) of 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5(4H)-one (I) of melting point 123°-125° C. were obtained.

Workup

  1. dissolutionWhen all of the product had dissolved
  2. customdid not exceed 30° C
  3. additionWhen the addition
  4. stirringthe reaction mixture was stirred at room temperature for a further 2 hours
  5. customThe reaction product which had precipitated
  6. filtrationwas then filtered off
  7. washwashed with 100 ml of water
  8. customdried

Sources & evidence

ORD record
ord-53610f69709e4224a28991821e0916b7
Source dataset
uspto-grants-1982_05
Patent number
US04328340

Linked notes

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