Pyridine → 4-[3-(2,5-Dichloro-4,6-dimethyl-3-pyridinyl)-1,2,4-oxadiazol-5-yl]-2-methoxy-6-nitrophenol

HRID 2274743Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]([Cl:13])=[C:8]([CH3:14])[C:3]=1/[C:4](=[N:6]/[OH:7])/[NH2:5].[OH:15][C:16]1[C:24]([O:25][CH3:26])=[CH:23][C:19]([C:20](Cl)=O)=[CH:18][C:17]=1[N+:27]([O-:29])=[O:28].N1C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:4]2[N:5]=[C:20]([C:19]3[CH:23]=[C:24]([O:25][CH3:26])[C:16]([OH:15])=[C:17]([N+:27]([O-:29])=[O:28])[CH:18]=3)[O:7][N:6]=2)=[C:8]([CH3:14])[C:9]([Cl:13])=[C:10]([CH3:12])[N:11]=1

Participants

Conditions

Temperature: 10 °C

Procedure

In a second vessel, (Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide (201.2 g, 1.24 eq) is suspended in 1,4-dioxane (720 mL, 4.5 vol) and the suspension is cooled to 10° C. The residue of example 3e in 1,4-dioxane is added slowly maintaining the temperature below 20° C. A clear orange solution is formed. After complete addition, the reaction mixture is stirred at 20° C. for 1 hour. Pyridine (483.7 mL, 8 eq) is then charged and the reaction mixture is heated slowly to 115° C. The mixture is stirred at 115° C. for 6 hours. The solution is then cooled to 20° C. Dioxane/pyridine is distilled off.

Workup

temperaturemaintaining the temperature below 20° C
customA clear orange solution is formed
additionAfter complete addition
temperaturethe reaction mixture is heated slowly to 115° C
stirringThe mixture is stirred at 115° C. for 6 hours
temperatureThe solution is then cooled to 20° C
distillationDioxane/pyridine is distilled off

Sources & evidence

ORD record: ord-9dc0f2a2f7ff42dbb01ab315dce023aa
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126988B2

Reaction notes

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