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

HRID 1708354Notes

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

Conditions

Temperature: 10 °C

Procedure

To a 100 mL 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

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

Sources & evidence

ORD record: ord-cc021e5c60bb45df9d89769527fe157a
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05358939

Reaction notes

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