Chloroselenobenzene → 2',4'-Dichloro-2-phenylselenenyl-2-(1H-1,2,4-triazol-1-yl)propiophenone

HRID 2290748Notes

Reaction equation

HRID 2290748 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH:10]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[CH3:11].[H-].[Na+].[C:20]1([Se:26]Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[C:10]([Se:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[CH3:11]

Participants

8

Reactant 4

HCID 21928ChloroselenobenzeneHCID 24758Sodium hydride2×HCID 516892Sodium BicarbonateHCID 28501531-Propanone, 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-

Product 1

HCID 867410802',4'-Dichloro-2-phenylselenenyl-2-(1H-1,2,4-triazol-1-yl)propiophenoneYield 47%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2',4'-dichloro-2-(1H-1,2,4-triazol-1-yl)propiophenone (3 g, 11 mMole) in tetrahydrofuran (60 ml) cooled to 5° was added sodium hydride as a 50% by weight dispersion in oil (0.68 g of said dispersion which contained 14 mMole of sodium hydride). Thirty minutes later phenylselenenyl chloride was added in four equal portions over five minutes (2.95 g, 15.4 mMole). Fifteen minutes later glacial acetic acid was added (1.5 ml) and the mixture was poured into water (100 ml). Excess solid sodium bicarbonate was added to basify the solution, which was then extracted with ethyl acetate (3×50 ml). The organic extracts were combined, washed with saturated saline solution (3×50 ml) and dried over anhydrous magnesium sulphate. Evaporation gave an impure oil, weight 5.4 g. Purification was carried out by `flash` column chromatography under slight pressure (2 p.s.i.) on a `Merck Kieselgel 60` (trade mark) 230-400 mesh silica-packed column, eluting with ether and 40°-60° petrol (1:1). The appropriate fractions after collection and evaporation gave a solid which was recrystallized from cyclohexane to give the pure title compound, 2.57 g, m.p. 84°-86° (47% yield).

Workup

  1. extractionwas then extracted with ethyl acetate (3×50 ml)
  2. washwashed with saturated saline solution (3×50 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customEvaporation
  5. customgave an impure oil, weight 5.4 g
  6. customPurification
  7. washeluting with ether and 40°-60° petrol (1:1)
  8. customThe appropriate fractions after collection and evaporation
  9. customgave a solid which
  10. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-4f4b6099580d42cd9e050b195ea63e7c
Source dataset
uspto-grants-1986_10
Patent number
US04618616

Reaction notes

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