Methyl iodide → Metribuzin

HRID 1447058Notes

Reaction equation

HRID 1447058 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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41.2 g (0.206 mol) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (VI) were introduced into a mixture of 200 g of 45% strength sodium hydroxide solution and 135 g of water, while stirring. After all of the product had dissolved, 34.0 g of methyl iodide were added in a manner such that the internal temperature did not rise above 30° C. When the addition had ended, the reaction mixture was stirred for a further 2 hours at room temperature. The reaction product which had precipitated was then filtered off, washed with 200 ml of water and dried. 35.6 g (81% 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. dissolutionAfter all of the product had dissolved
  2. customdid not rise above 30° C
  3. additionWhen the addition
  4. stirringthe reaction mixture was stirred for a further 2 hours at room temperature
  5. customThe reaction product which had precipitated
  6. filtrationwas then filtered off
  7. washwashed with 200 ml of water
  8. customdried

Sources & evidence

ORD record
ord-9281a138bc914af690873fb50f323e75
Source dataset
uspto-grants-1982_02
Patent number
US04315094

Reaction notes

Loading…