Potassium Iodide → HCID 23447401, compound

HRID 2186182Notes

Reaction equation

HRID 2186182 reaction equation
Cl[CH2:2][S:3]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[C:8](=[O:21])[CH2:7]1)(=[O:5])=[O:4].[Cl:22][C:23]1[CH:30]=[C:27]([CH:28]=O)[C:26]([OH:31])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[O:31][C:2]([S:3]([N:6]3[CH2:11][CH2:10][N:9]([CH2:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=4)[C:8](=[O:21])[CH2:7]3)(=[O:5])=[O:4])=[CH:28][C:27]=2[CH:30]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 23447429HCID 23447429, compound

Product 1

HCID 23447401HCID 23447401, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloromethylsulfonyl-1-(4-cyanobenzyl)-2-piperazinone (3.20 g), 5-chlorosalicylaldehyde (2.29 g), potassium carbonate (1.48 g), potassium iodide (1.62 g) and DMF (80 ml) was stirred at 80° C. for 2 days. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to give colorless crystals of the title compound (384 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a53100f67777487dbdf667161bf932bc
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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