Methyl iodide → HCID 21277244, compound

HRID 2292232Notes

Reaction equation

HRID 2292232 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:4]=[C:3]1[S:15][CH3:16].[CH3:17]I.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:17][NH:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:4]=[C:3]1[S:15][CH3:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 122957854-Amino-3-methylthio-6-phenyl-1,2,4-triazine-5-one

Product 1

HCID 21277244HCID 21277244, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A two-phase mixture of 35.1 g (0.15 mole) of 4-amino-3-methylthio-6-phenyl-4H-1,2,4-triazin-5-one, 24.4 ml (0.375 mole) of methyl iodide, 5 g of tetrabutylammonium bromide, 200 ml of toluene and 60 ml of a 50% solution of sodium hydroxide is efficiently stirred for 2 hours, the temperature rising from 20° to 40° C. The organic phase is separated and filtered over silica gel. Evaporation of the filtrate yields 25.1 g (67.5% of theory) of 4-methylamino-3-methylthio-6-phenyl-4H-1,2,4-triazin-5-one which melts at 119°-120° C.

Workup

  1. customrising from 20° to 40° C
  2. customThe organic phase is separated
  3. filtrationfiltered over silica gel
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-965c073f2e43416680ed240e49acb73c
Source dataset
uspto-grants-1989_01
Patent number
US04801708

Reaction notes

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