Sodium Sulfite → 2',4'-Dichloro-2-(1H-1,2,4-triazol-1-yl)prop-2-enophenone

HRID 2290749

Reaction equation

HRID 2290749 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:24])[C:10]([Se]C1C=CC=CC=1)([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[CH3:11].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:24])[C:10]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)=[CH2:11]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86741080HCID 86741080, compound

Product 1

HCID 212946112',4'-Dichloro-2-(1H-1,2,4-triazol-1-yl)prop-2-enophenoneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Part (B) (0.42 g, 1.0 mMole) in methylene chloride (5 ml) at -72° was added m-chloroperbenzoic acid (0.32 g, 1.5 mMole) in three equal portions over a twelve minute period. Two hours later the mixture, at -70°, was poured into an aqueous solution of saturated sodium bicarbonate and sodium sulphite (20 ml) with vigorous stirring. The organic layer was separated, washed with saturated sodium bicarbonate (3×5 ml) and water (3×5 ml), and dried over anhydrous sodium sulphate. Evaporation gave the title compound as an oil, 0.20 g, (74% yield). The compound was used directly in the next stage.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated sodium bicarbonate (3×5 ml) and water (3×5 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation

Sources & evidence

ORD record
ord-6ca793413b8342d5a2996ac8b9542a09
Source dataset
uspto-grants-1986_10
Patent number
US04618616

Linked notes

Loading…