Methyl iodide → 6-(1-Cyclopropylethyl)-4-methylamino-3-methylthio-1,2,4-triazin-5(4H)-one

HRID 231389Notes

Reaction equation

HRID 231389 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([CH:9]([CH:11]2[CH2:13][CH2:12]2)[CH3:10])=[N:5][N:4]=[C:3]1[S:14][CH3:15].[CH3:16]I.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:11]1([CH:9]([C:6]2[C:7](=[O:8])[N:2]([NH:1][CH3:16])[C:3]([S:14][CH3:15])=[N:4][N:5]=2)[CH3:10])[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 144026044-Amino-6-(1-cyclopropylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one

Product 1

HCID 144026096-(1-Cyclopropylethyl)-4-methylamino-3-methylthio-1,2,4-triazin-5(4H)-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

100 ml of toluene and 56.5 g (0.25 mol) of 4-amino-6-(1-cyclopropylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one, and then 89.5 g (0.63 mol) of methyl iodide and 8.5 g (0.025 mol) of tetrabutylammonium bromide are added to 100 ml of 50% strength aqueous sodium hydroxide solution with vigorous stirring. The emulsion is stirred vigorously until the exothermic reaction abates (temperature rise to 50° C.). The mixture is filtered with suction through a glass frit at 20° C., the phases are separated and the organic phase is evaporated. The residue is recrystallized from methyl tert.-butyl ether. 32.9 g of the above compound of melting point 66°-68° C., identical with a product prepared according to process A (cf. Example 5), are obtained.

Workup

  1. custom(temperature rise to 50° C.)
  2. filtrationThe mixture is filtered with suction through a glass frit at 20° C.
  3. customthe phases are separated
  4. customthe organic phase is evaporated
  5. customThe residue is recrystallized from methyl tert.-butyl ether
  6. custom32.9 g of the above compound of melting point 66°-68° C., identical with a product prepared
  7. customare obtained

Sources & evidence

ORD record
ord-82f2d5a396f449c99f1a75c5a187532d
Source dataset
uspto-grants-1989_07
Patent number
US04846881

Reaction notes

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