Sodium Iodide → HCID 18317595, compound

HRID 1700641Notes

Reaction equation

HRID 1700641 reaction equation
CC1C=CC(S([NH:11][NH:12][C:13]2[CH2:18][CH:17]([C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[CH2:16][C:15](=[O:24])[CH:14]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:32][C:33](=O)[CH3:34].[I-].[Na+]>COCCOC.C(O)C>[CH3:34][C:33]1[C:14]2[C:15](=[O:24])[CH2:16][CH:17]([C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[CH2:18][C:13]=2[N:12]=[N:11][CH:32]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 18317687HCID 18317687, compound

Product 1

HCID 18317595HCID 18317595, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[2-(4-methylphenylsulfonyl)hydrazino]-5-(thiophen-3-yl)cyclohexen-3-one (3.62 g), anhydrous potassium carbonate (3.45 g), chloroacetone (1.15 g), sodium iodide (1 g), ethanol (50 ml) and 1,2-dimethoxyethane (20 ml) was stirred at 80° C. for 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified with silica gel column chromatography. The resulting crystals were recrystallized from ethyl acetate-hexane to give 4-methyl-7-(thiophen-3-yl)-5,6,7,8-tetrahydrocinnolin-5-one (0.8 g) as yellow crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified with silica gel column chromatography
  5. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8ac69261108f49a3bc7abc7635dafb16
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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