Methyl iodide → HCID 15114607, compound

HRID 1089448Notes

Reaction equation

HRID 1089448 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[N:11][NH:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:23]I>C(O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9](=[O:20])[N:10]([CH3:23])[N:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15114606HCID 15114606, compound

Product 1

HCID 15114607HCID 15114607, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, room temperature, suspension of 4-benzyl-5-(4-chlorophenyl)-3H-1,2,4-triazol-3-one (10.85 g, 3.797×10-2 mole), 1 molar aqueous NaOH (42 ml, 4.2×10-2 mole), and ethanol (15 ml) was added methyl iodide (3.6 ml, 5.8×10-2 mole). After stirring overnight, the reaction was transferred to a separatory funnel where it was extracted with EtOAc (3x). The EtOAc extracts were combined, washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a yellowish foam. Purification of this foam by a combination of flash chromatography (20% EtOAc/CH2Cl2) and crystallization from cyclohexane afforded colorless crystals 5.92 g (52%), mp 90°-91° C.

Workup

  1. customthe reaction was transferred to a separatory funnel
  2. extractionwhere it was extracted with EtOAc (3x)
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe drying agent was removed by filtration
  6. customthe filtrate was evaporated at reduced pressure
  7. customleaving a yellowish foam
  8. customPurification of this foam
  9. customby a combination of flash chromatography (20% EtOAc/CH2Cl2) and crystallization from cyclohexane afforded colorless crystals 5.92 g (52%), mp 90°-91° C.

Sources & evidence

ORD record
ord-e521242269c342b5a64e8ac42e542b6f
Source dataset
uspto-grants-1990_10
Patent number
US04966909

Reaction notes

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