Sodium Iodide → HCID 18317647, compound

HRID 1700693Notes

Reaction equation

HRID 1700693 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13]([NH:15][NH:16]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:12][C:11](=[O:27])[CH2:10]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:35][C:36](=O)[CH3:37].[I-].[Na+]>COCCOC.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13]2[N:15]=[N:16][CH:35]=[C:36]([CH3:37])[C:12]=2[C:11](=[O:27])[CH2:10]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium Carbonate2×HCID 18317326HCID 18317326, compound

Product 1

HCID 18317647HCID 18317647, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 5-(2,5-dichlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.65 g), anhydrous potassium carbonate (0.696 g), methanol (10 ml) and 1,2-dimethoxyethane (8 ml) were added under ice-cooling 1-chloropropan-2-one (0.465 g) and sodium iodide (0.15 g), and the mixture was stirred at room temperature for 2 hours. To the mixture was added anhydrous potassium carbonate (0.64 g), and the mixture was stirred for 3 hours at 80° C. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate (70 ml) and water (30 ml). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 7-(2,5-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (0.253 g) as yellowish brown oil.

Workup

  1. additionwere added under ice-
  2. stirringthe mixture was stirred for 3 hours at 80° C
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue was added ethyl acetate (70 ml) and water (30 ml)
  5. stirringThe mixture was shaken
  6. washthe separated upper layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-e881247fc3e14f178d7f9291d3ac098f
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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