Methyl iodide → HCID 135727125, compound

HRID 456405Notes

Reaction equation

HRID 456405 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[OH-].[Na+].[CH3:15]I>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])=[N:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13554453051449-77-5

Product 1

HCID 135727125HCID 135727125, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 2-(2H-1,2,3,4-tetraazol-5-yl)phenol (0.486 g, 3 mmol) and sodium hydroxide (NaOH) (72 mg, 3 mmol) in water (15 mL) a solution of tetrabutylammonium chloride (83 mg, 0.3 mmol) was added. The mixture was stirred for 5 min, then methyl iodide (0.425 g, 0.187 mL, 3 mmol) was added, and the mixture was stirred for 6 days. The organic layer was then separated, washed with water (2×15 mL), and dried. Evaporation of solvent and flash chromatography on silica gel (ethyl acetate/heptane, 1:1) afforded the subtitle compound (0.257 g, 49%).

Workup

  1. stirringthe mixture was stirred for 6 days
  2. customThe organic layer was then separated
  3. washwashed with water (2×15 mL)
  4. customdried
  5. customEvaporation of solvent and flash chromatography on silica gel (ethyl acetate/heptane, 1:1)

Sources & evidence

ORD record
ord-1d03e42a01084f3088ba775d90883bb6
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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