Methyl iodide → HCID 14880637, compound

HRID 1461627Notes

Reaction equation

HRID 1461627 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[N:5][N:4]=[C:3]1[S:14][CH3:15].[OH-].[Na+].[CH3:18]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:18][NH:1][N:2]1[C:7](=[O:8])[C:6]([CH:9]([CH2:10][CH3:11])[CH2:12][CH3:13])=[N:5][N:4]=[C:3]1[S:14][CH3:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13458077HCID 13458077, compound

Product 1

HCID 14880637HCID 14880637, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

4.2 g (0.018 mol) of 4-amino-3-methylthio-6-(pent-3-yl)-1,2,4-triazin-5(4H)-one are introduced at room temperature into a mixture of 7.5 ml of 45% strength sodium hydroxide solution and 7.5 ml of toluene. 7.1 g (0.05 mol) of methyl iodide and 0.6 g of tetrabutylammonium bromide are then added all at once at room temperature. The mixture is stirred vigorously, and the temperature rises from 21° C. to 31° C. Stirring of the reaction mixture is continued for 1 hour, and the organic top phase is then removed in a separation funnel and stirred in 100 ml of water. The mixture is extracted with methylene chloride (three times, using 70 ml each time) and then filtered over silica gel, which, after concentrating, gives 3.8 g (87% of theory) of 4-methylamino-3-methylthio-6-(pent-3-yl)-1,2,4-triazin-5-(4H}-one as a colorless oil of refractive index nD20 =1.553.

Workup

  1. customrises from 21° C. to 31° C
  2. stirringStirring of the reaction mixture
  3. customthe organic top phase is then removed in a separation funnel
  4. stirringstirred in 100 ml of water
  5. extractionThe mixture is extracted with methylene chloride (three times, using 70 ml each time)
  6. filtrationfiltered over silica gel, which
  7. concentrationafter concentrating

Sources & evidence

ORD record
ord-5251c3288c8e4e8c8a9d521d29718bd3
Source dataset
uspto-grants-1991_12
Patent number
US05076833

Reaction notes

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