Sodium Cyanide → 1-Cyano-2-(2,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanol

HRID 728328Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.[C-:18]#[N:19].[Na+]>CN(C)C=O.O>[C:18]([CH2:11][C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([OH:10])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)#[N:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (6.7 g) in dimethylformamide (198 ml) at 60° C. was added dropwise over 25 minutes a solution of sodium cyanide (2.84 g) in water (49 ml). Heating at 60° C. was continued for five hours. The reaction mixture was then cooled, poured into water (900 ml), and extracted with ethyl acetate (3×150 ml). The combined organic extracts were washed with saturated aqueous brine, dried (Na2SO4 ) and evaporated to dryness to give a pale yellow solid (6.1 g) which was triturated with ethyl ether. The residual solid was recrystallized from ethyl ether/methanol to give the title compound, 4.13 g (56%), m.p. 217°-219° C.

Workup

temperatureThe reaction mixture was then cooled
extractionextracted with ethyl acetate (3×150 ml)
washThe combined organic extracts were washed with saturated aqueous brine
dry with materialdried (Na2SO4 )
customevaporated to dryness

Sources & evidence

ORD record: ord-0f11cbbe3f8a4f6c90dcd388cdaf9625
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047548

Reaction notes

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