Water → HCID 10160441, compound

HRID 1007562Notes

Reaction equation

HRID 1007562 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][N:8]=2)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:21]#[N:22].[CH2:23]=[C:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.[F-].[K+].O>CS(C)=O>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:2]([O:31][CH2:30][CH:27]3[CH2:28][CH2:29][C:24](=[CH2:23])[CH2:25][CH2:26]3)=[C:3]([C:21]#[N:22])[C:4]([C:17]([F:20])([F:19])[F:18])=[N:5]2)=[N:8][CH:9]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 138604-MethylenecyclohexylmethanolHCID 522689Potassium FluorideHCID 12135150HCID 12135150, compound

Product 1

HCID 10160441HCID 10160441, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile (0.35 g, 1 mmol) and (4-methylene-cyclohexyl)-methanol (0.252 g, 2 mmol) were dissolved in dry dimethylsulfoxide (DMSO) (5 ml) and potassium fluoride (0.116 g, 2 mmol) was added to the clear solution. The resulting mixture was stirred at 20° for a period of 48 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (50 ml) and the resulting mixture was extracted with ethyl acetate (20 ml). The organic extract was dried over magnesium sulfate and concentrated with a rotary evaporator. The desired product (0.3 g, 68%) was isolated by chromatography on silica gel eluting with a solution of 15% of ethyl acetate and 15% of acetone in hexane. MS: 440, r.t.: 3.0.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (20 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-8d9ab7bd44374d7886b8846bcb39788b
Source dataset
uspto-grants-2004_09
Patent number
US06794512B2

Reaction notes

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