Methyl iodide → Metribuzin

HRID 1439439Notes

Reaction equation

HRID 1439439 reaction equation
[C:1]([C:5]1[C:6](=[O:13])[N:7]([NH2:12])[C:8]([SH:11])=[N:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14]I>[OH-].[Na+].CO>[C:1]([C:5]1[C:6](=[O:13])[N:7]([NH2:12])[C:8]([S:11][CH3:14])=[N:9][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178441961HCID 178441961, compound

Product 1

HCID 30479MetribuzinYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

4 parts by weight of 6-tert.-butyl-3-mercapto-4-amino-1,2,4-triazin-5(4H)-one are dissolved in a mixture of 11 parts by weight of 2-normal sodium hydroxide and 4 parts by weight of methanol and the solution is treated at 0° C with 3.2 parts by weight of methyl iodide. The reaction mixture is then stirred for a further 4 hours at 20° C. The reaction product crystallizes out and is filtered off, dried and recrystallized from benzene. 3.52 parts by weight of 6-tert.-butyl-3-methylthio-4-amino-1,2,4-triazin-5(4H)-one of melting point 126°-127° C are obtained Yield: 82% of theory.

Workup

  1. customThe reaction product crystallizes out
  2. filtrationis filtered off
  3. customdried
  4. customrecrystallized from benzene

Sources & evidence

ORD record
ord-e68b40369e854e7ab5ddf1801ba43fb5
Source dataset
uspto-grants-1977_11
Patent number
US04059634

Reaction notes

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