Methyl iodide → Metribuzin

HRID 1763878Notes

Reaction equation

HRID 1763878 reaction equation
[SH:1][C:2]1[N:7]([NH2:8])[C:6](=[O:9])[C:5]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][N:3]=1.[CH3:14]I>[OH-].[Na+].CO>[CH3:14][S:1][C:2]1[N:7]([NH2:8])[C:6](=[O:9])[C:5]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][N:3]=1

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 3-mercapto-4-amino-6tert.-butyl-1,2,4-triazin-5-(4H)-one are dissolved in a mixture of 11 parts by weight of 2 normal sodium hydroxide solution 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 at 20° C for a further 4 hours. The reaction product crystallizes out, is filtered off, dried and recrystallized from benzene. 3.52 parts by weight of 3-methylthio-4-amino-6-tert.-butyl-1,2,4-triazin-5(4H)-one (XV) of melting point 126°-127° 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-82ca29777c3d4bbba0045e55927e3e38
Source dataset
uspto-grants-1978_09
Patent number
US04113767

Reaction notes

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