Methyl iodide → 1-[2-(4-Chlorophenyl)-2-(methoxymethyl)hexyl]-1,2,4-triazole

HRID 2211094Notes

Reaction equation

HRID 2211094 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][OH:12])=[CH:6][CH:5]=1.[CH3:23]I>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:11][O:12][CH3:23])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 157666652-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol

Product 1

HCID 199569461-[2-(4-Chlorophenyl)-2-(methoxymethyl)hexyl]-1,2,4-triazoleYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

To a 100mL 3 neck flask stirring under nitrogen was charged 0.40 g (0.010 mole) of 60% sodium hydride, prewashed with hexanes, in 30 mL of dimethylformamide. The slurry was cooled to 10° C. and 2.12 g (0.00723 mole) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol in 15 mL of dimethylformamide was added over 15 minutes. The reaction was warmed to room temperature and 1.17 g (0.00812 mole) of methyl iodide was added directly and the reaction was stirred overnight at room temperature. The reaction was quenched with 10 mL water and 100 mL ether. The organic phase was washed with 2×25 mL water, dried, concentrated and gave 1.53 g (69% yield) of product as an oil.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. customThe reaction was quenched with 10 mL water and 100 mL ether
  3. washThe organic phase was washed with 2×25 mL water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ed9df671b654b38b42698c64299d8e3
Source dataset
uspto-grants-1995_10
Patent number
US05462931

Reaction notes

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