Sodium Iodide → HCID 21952553, compound

HRID 1263454Notes

Reaction equation

HRID 1263454 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].C(#N)C.[CH2:11]([N:13]1[C:22]2[CH:21]=[CH:20][C:19]([CH:23]([CH3:25])[CH3:24])=[CH:18][C:17]=2[C:16](=[O:26])[C:15]2[C:27](O)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[C:33]([C:14]1=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:12].S([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[CH2:11]([N:13]1[C:22]2[CH:21]=[CH:20][C:19]([CH:23]([CH3:25])[CH3:24])=[CH:18][C:17]=2[C:16](=[O:26])[C:15]2[CH:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[C:33]([C:14]1=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:12]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 24437Sodium SulfiteHCID 21952555HCID 21952555, compound

Product 1

HCID 21952553HCID 21952553, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of trimethylsilyl chloride (0.19 mL, 1.5 mmol), sodium iodide (224 mg, 1.5 mmol) and acetonitrile (61 mg, 1.5 mmol) was added dropwise a solution of 5-ethyl-8-isopropyl-11-hydroxy-11-phenyl-5,10-dihydro-11H-indeno[1,2-b]quinolin-10-one in 1,2-dichloroethane with stirring at room temperature. The mixture was stirred at 50° C. overnight followed by allowing to cool to room temperature. The reaction mixture was treated diluted aqueous solution of sodium sulfite. The separated organic layer was washed with water four times and then with saturated sodium chloride solution followed by drying with sodium sulfate. After removing the solvent, the residue was purified by silica gel-chromatography (chloroform) followed by crystallization from diethyl ether to give the title compound. 1H-NMR(CDCl3) δ 1.30(6H,d,CH(CH3)2), 1.79(3H,t,NCH2CH3), 3.05(1H,septet,CH), 4.81(2H,q,NCH2), 5.18(1H,s,H-11), 7.16-7.64(10H,m,Ar-H), 7.96(1H,d,H-6), 8.37(1H,d,H-9)

Workup

  1. stirringThe mixture was stirred at 50° C. overnight
  2. temperatureto cool to room temperature
  3. washThe separated organic layer was washed with water four times
  4. dry with materialby drying with sodium sulfate
  5. customAfter removing the solvent
  6. customthe residue was purified by silica gel-chromatography (chloroform)
  7. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-e90dd463c1504faa8051d2e44859d2b9
Source dataset
uspto-grants-2003_04
Patent number
US06541470B1

Reaction notes

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