Water → 2-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile

HRID 1621152Notes

Reaction equation

Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[C:8]1([N:7]2[C:3]([CH2:2][C:20]#[N:21])=[N:4][C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-(bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole (265 mg, 843 μmol) and potassium cyanide (62.3 mg, 928 μmol) in DMSO (5 mL) was heated at 60° C. for 1.5 h. The reaction mixture was cooled to RT, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (2×25 mL) and brine (1×25 mL), and the combined organic layer was dried over MgSO4 and concentrated in vacuo to give 251 mg of crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow waxy solid (120 mg, 461 μmol, 54.7%).

Workup

temperatureThe reaction mixture was cooled to RT
extractionextracted with ethyl acetate (2×50 mL)
washThe organic phases were washed with water (2×25 mL) and brine (1×25 mL)
dry with materialthe combined organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e3262c180684443d9049f7f3ab1c54a5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772510B2

Reaction notes

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