1H-1,2,4-Triazole → HCID 14798969, compound

HRID 345861Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[H][H].[C:11]([C:19]1([C:22]#[N:23])[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1>CS(C)=O>[C:22]([C:19]1([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:18])[CH2:4][N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH2:21][CH2:20]1)#[N:23]

Participants

Conditions

Temperature: 40 °C

Procedure

660 mg (0.022 mol) of (80% in oil) sodium hydride are suspended in 30 ml of abs. DMSO under argon. 4.8 g (0.022 mol) of trimethylsulphoxonium iodide (EGA) are added at RT and the mixture is stirred until evolution of hydrogen has ended. 3.4 g (20 mmol) of 1-benzoyl-1-cyanocyclopropane in 10 ml of abs. DMSO are then added rapidly. The mixture is stirred for 2 h at 40° C. and 2 g (30 mmol) of sublimed 1,2,4-triazole and 908 mg (10 mmol) of 1,2,4-triazole-Na salt (EGA) are then added. The mixture is stirred for 2 h at 50° C. and for 4 h at 80° C., cooled, stirred into ice-water and extracted with chloroform. The organic phase is washed with 2N NaOH, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel using ethyl acetate and the product is recrystallized from dichloromethane/petroleum ether. 2 g (40% of theory) of 1-(1-cyanocyclopropyl)-1-phenyl-2-(1,2,4-triazol-1-yl)ethanol having a melting point of 103°-105° C. are obtained as colorless crystals,

Workup

stirringThe mixture is stirred for 2 h at 50° C. and for 4 h at 80° C.
temperaturecooled
extractionextracted with chloroform
washThe organic phase is washed with 2N NaOH
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel
customthe product is recrystallized from dichloromethane/petroleum ether

Sources & evidence

ORD record: ord-3bfc0e24c5604a87960fcf6211fe9f8d
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05059615

Reaction notes

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