1H-1,2,4-Triazole → HCID 14798970, compound

HRID 345862Notes

Reaction equation

HRID 345862 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[H][H].[F:11][C:12]1[CH:24]=[CH:23][C:15]([C:16]([C:18]2([C:21]#[N:22])[CH2:20][CH2:19]2)=[O:17])=[CH:14][CH:13]=1.[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1>CS(C)=O>[C:21]([C:18]1([C:16]([C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:24][CH:23]=2)([OH:17])[CH2:2][N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)[CH2:20][CH2:19]1)#[N:22]

Participants

7

Reactant 5

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 14798951HCID 14798951, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14798970HCID 14798970, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
40 °C

Procedure

2.42 g (11 mmol) of trimethylsulphoxonium iodide (EGA) are added in portions at 20° C. to a suspension of 0.33 g (11 mmol) of sodium hydride (80% in oil) in 20 ml of DMSO p.a. The mixture is stirred until evolution of hydrogen has ended and 2 g (10mmol) of (4-fluoro)-1-benzoyl-1-cyanocyclopropane, dissolved in 5 ml of abs. DMSO, are rapidly added dropwise. The mixture is stirred for 1 h at RT and for 1 h at 40° C., then 1.04 g (15 mmol) of 1,2,4-triazole (sublimed) and 0.46 g (5 mmol) of 1,2,4-triazole Na salt in DMSO are added. The mixture is stirred for 2 h at 50° C. and for 4 h at 80° C., poured into ice-water and extracted using dichloromethane. The organic phase is washed with 2N sodium hydroxide solution, dried over Na2SO4 and concentrated. The residue is chromatographed on silica gel and the product is crystallized from diethyl ether. 1.2 g (44% of theory) of colorless crystals of 1-(1-cyanocyclopropyl)-1-(4-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanol are thus obtained having a melting point of 121°-122° C.,

Workup

  1. stirringThe mixture is stirred for 2 h at 50° C. and for 4 h at 80° C.
  2. extractionextracted
  3. washThe organic phase is washed with 2N sodium hydroxide solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel
  7. customthe product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-7ee8b58ee5f74a96ad37b8f57f969be3
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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