Dimethylformamide → HCID 10268378, compound

HRID 584755Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([OH:22])=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.C(OCC)(=O)C.Br[CH2:41][F:42]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([O:22][CH2:41][F:42])=[N:10]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol (0.3 g, 1.01 mmol) and potassium carbonate (418 mg, 3.03 mmol) in bromofluoromethane (1 mL)-dimethylformamide (3 mL) was heated at 100° C. with stirring for 3.5 hours. After cooling, ethyl acetate and water were poured into the mixture. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate). The desired product was triturated with hexane, isolated by filtration, and dried in vacuo to give 1,5-bis(4-methoxyphenyl)-3-(fluoromethoxy)-1H-1,2,4-triazole.

Workup

temperatureAfter cooling
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
customThe desired product was triturated with hexane
customisolated by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-7a07756b601048f8a8e577d392ff76a2
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927230B2

Reaction notes

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