Sodium hydride → 2-[3-(4-Cyanostyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl methyl)ethanol

HRID 1650796Notes

Reaction equation

[H-].[Na+].[C:3]([C:5]1[CH:17]=[CH:16][C:8]([CH:9]=[CH:10][C:11]2[N:15]=[CH:14][NH:13][N:12]=2)=[CH:7][CH:6]=1)#[N:4].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]1([O:34][CH2:33]1)[CH2:27][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CN(C)C=O.O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[CH:10][C:11]2[N:15]=[CH:14][N:13]([CH2:33][C:26]([C:20]3[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=3[F:18])([CH2:27][N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)[OH:34])[N:12]=2)=[CH:16][CH:17]=1)#[N:4]

Participants

Conditions

Temperature: 75 °C

Procedure

Sodium hydride (55% oil dispersion) (0.4 g.) was added to a solution of 3-(4-cyanostyryl)-1,2,4-triazole (1.6 g.) in dimethylformamide (20 ml.). After the effervescence had ceased, a solution of 2-(2,4-difluorophenyl)-2,3-epoxy-1-(1,2,4-triazol-1-yl)propane (1.9 g.) in dimethylformamide (10 ml.) was added, and the mixture was heated at 75° C. for 5 hours, then stirred at room temperature for 16 hours. The reaction mixture was diluted with water (150 ml.) and extracted with ethyl acetate (100 ml). The organic layer was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was crystallised from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) to give 2-[3-(4-cyanostyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl methyl)ethanol, m.p. 189°-91° C.

Workup

extractionextracted with ethyl acetate (100 ml)
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulphate
customevaporated to dryness
customThe residue was crystallised from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record: ord-da0360a4b79e4fc09b5dd932d74ec914
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04925863

Reaction notes

Loading…