Methyl iodide → HCID 15586382, compound

HRID 2290366Notes

Reaction equation

HRID 2290366 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]=[C:5]([CH3:9])[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3]1.[CH3:16][Mg]I.CI.[Mg].[Cl-].[NH4+]>C1C=CC=CC=1.C(OCC)C>[C:10]1([C:4]2[C:5]([CH3:16])([CH3:9])[NH:6][C:7](=[O:8])[N:2]([CH3:1])[N:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20232030HCID 20232030, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 15586382HCID 15586382, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A hot solution of 2,5-dimethyl-6-phenyl-1,2,4-triazin-3(2H)-one (5 g) in benzene (60 ml) was added dropwise to a stirred solution of methylmagnesium iodide prepared from methyl iodide (17.5 g) and magnesium turnings (3 g) in diethyl ether (80 ml) at room temperature. The solution was refluxed under heating for 40 minutes and then allowed to stand for 1 hour at room temperature. The solution was treated with a saturated aqueous solution of ammonium chloride to decompose excess Grignard reagent. The organic layer was separated, dried over magnesium sulfate, treated with activated charcoal, and evaporated to dryness. The resultant solid was recrystallized from a mixture of diispropyl ether and chloroform to give 6-phenyl-2,5,5-trimethyl-4.5-dihydro-1,2,4-triazin-3(2H)-one (4.21 g), m.p. 128°~130° C.

Workup

  1. temperatureThe solution was refluxed
  2. temperatureunder heating for 40 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with activated charcoal
  6. customevaporated to dryness
  7. customThe resultant solid was recrystallized from a mixture of diispropyl ether and chloroform

Sources & evidence

ORD record
ord-5b5bcaa1052343f6abd1f327e8024fd6
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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