Pyridine → HCID 22934555, compound

HRID 1354445Notes

Reaction equation

Cl.[C:2](=[NH:11])(OC)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:12][NH:13][NH2:14].Cl[C:16]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=O.N1C=CC=CC=1>CO.O>[CH3:12][N:13]1[C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:11][C:16]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[N:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution (20 ml) of methyl benzimidate hydrochloride (2.00 g) in methanol was added methylhydrazine (0.540 g) at 0° C. This mixture was stirred at 0° C. for 1 hr., and at room temperature for 2 hrs., and concentrated. The residue was washed with ether to give colorless crystals. A mixture of these crystals, methyl 4-chloroformylbenzoate (2.32 g) and pyridine (30 ml) was heated under reflux for 1 hr. and poured into iced water. The crystals were collected by filtration and purified by silica gel column chromatography (hexane:ethyl acetate=2:1, volume ratio) to give methyl 4-(1-methyl-5-phenyl-1H-1,2,4-triazol-3-yl)benzoate (1.50 g, yield 44%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: 167–168° C.

Workup

wait, and at room temperature for 2 hrs
concentration, and concentrated
washThe residue was washed with ether
customto give colorless crystals
temperaturewas heated
temperatureunder reflux for 1 hr
filtrationThe crystals were collected by filtration
custompurified by silica gel column chromatography (hexane:ethyl acetate=2:1, volume ratio)

Sources & evidence

ORD record: ord-f5f85f8d85c346ffa8e183a0baa3e8ab
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223791B2

Reaction notes

Loading…