Potassium Cyanide → 2-(1-Chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-thiocyanato-1,2,4-triazol-1-yl)-propan-2-ol

HRID 1276420Notes

Reaction equation

ClCl.[Cl:3][C:4]1([C:7]([OH:23])([CH2:16][N:17]2[C:21]([SH:22])=[N:20][CH:19]=[N:18]2)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[CH2:6][CH2:5]1.[C-:24]#[N:25].[K+]>C(O)(=O)C.ClCCl>[Cl:3][C:4]1([C:7]([OH:23])([CH2:16][N:17]2[C:21]([S:22][C:24]#[N:25])=[N:20][CH:19]=[N:18]2)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 20 °C

Procedure

At 20° C., chlorine gas is introduced into a mixture of 1.72 g (5 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol and 0.65 g (10 mmol) of potassium cyanide in 20 ml of acetic acid. The reaction mixture is stirred at 20° C. for 20 hours and then diluted with dichloromethane. The mixture is then extracted repeatedly with dilute aqueous sodium hydroxide solution and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The product that remains is purified over silica gel using petroleum ether/ethyl acetate=1:1 as mobile phase. Concentration of the eluate gives 1.2 g (64% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-thiocyanato-1,2,4-triazol-1-yl)-propan-2-ol in the form of an oil.

Workup

extractionThe mixture is then extracted repeatedly with dilute aqueous sodium hydroxide solution
dry with materialthe organic phase is dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe product that remains is purified over silica gel

Sources & evidence

ORD record: ord-a268c1ea0396449d817701adae346bd2
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166059

Reaction notes

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