Methyl iodide → MDL 27266

HRID 1648246Notes

Reaction equation

HRID 1648246 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH3:15])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:18]I>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:14][CH3:15])[C:10](=[O:13])[N:11]([CH3:18])[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 357933H-1,2,4-Triazol-3-one, 5-(4-chlorophenyl)-4-ethyl-2,4-dihydro-

Product 1

HCID 60655MDL 27266

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, room temperature solution of 5-(4-chlorophenyl) -2,4-dihydro-4-ethyl-3H-1,2,4-triazol-3-one (6.00 g, 2.68×10-2 mole) and 1 molar aqueous NaOH (30.0 ml, 3.00×10-2 mole) was added a solution of methyl iodide (2.5 ml, 4.0×10-2 mole) and ethanol (10 ml). After stirring overnight at room temperature, the reaction mixture was transferred to a separatory funnel where it was extracted three times with EtOAc. The EtOAc extracts were combined, washed with saturated aqueous NaCl, and dried over Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving an oil which slowly solidified. Chromatography and crystallization from cyclohexane gave small colorless needles: 3.4 g (53%), Mp 73°-75° C.

Workup

  1. customthe reaction mixture was transferred to a separatory funnel
  2. extractionwhere it was extracted three times with EtOAc
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. customThe drying agent was removed by filtration
  6. customthe filtrate was evaporated at reduced pressure
  7. customleaving an oil which
  8. customChromatography and crystallization from cyclohexane
  9. customgave small colorless needles

Sources & evidence

ORD record
ord-e815199bb4ce4f28bdc9f8bb453a266e
Source dataset
uspto-grants-1995_07
Patent number
US05436252

Reaction notes

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