4-Methoxybenzylamine → 5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenol

HRID 2081112Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[OH:14].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>ClCCl>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:22]2[C:10]([CH3:13])=[N:11][N:12]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([OH:14])[CH:4]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 152.5 °C

Procedure

A mixture of 2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol (0.65 g; 3.42 mmol) (from Example 11 supra) and 4-methoxybenzylamine (3.10 g; 22.6 mmol) (Aldrich) in a sealed reaction vessel was heated in an oil bath at 150-155° C. for 42 hours. The reaction mixture was cooled to room temperature and diluted with dichloromethane and hexanes, forcing the product to precipitate out of solution. The crude solid was collected by filtration and then precipitated again from a dichloromethane-methanol solution as the solvent was evaporated off. The solid was collected and dried, to give 5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenol. (Yield 0.849 g, 76.3%).

Workup

customin a sealed reaction vessel
temperatureThe reaction mixture was cooled to room temperature
customto precipitate out of solution
filtrationThe crude solid was collected by filtration
customprecipitated again from a dichloromethane-methanol solution as the solvent
customwas evaporated off
customThe solid was collected
customdried

Sources & evidence

ORD record: ord-d3e3faa4c9d74befbf04c99d94123eb4
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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