Methyl iodide → 5,6-dihydro-6-methylthio-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341844Notes

Reaction equation

HRID 341844 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]2[N:21]3[C:22]4[C:17]([CH:18]([SH:23])[CH2:19][CH2:20]3)=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:24]I>O1CCCC1>[CH3:24][S:23][CH:18]1[C:17]2[C:22]3=[C:13]([N:12]=[C:11]([CH2:10][CH2:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:21]3[CH2:20][CH2:19]1)[CH:14]=[CH:15][CH:16]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 158384715,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiol

Product 1

HCID 158384725,6-dihydro-6-methylthio-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The mixture of 60% sodium hydride (245 mg) and anhydrous tetrahydrofuran (20 mL) under an argon atmosphere was added dropwise the solusion of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiol (0.45 g) obtained in Example 28 in anhydrous tetrahydrofuran (20 mL) at room temperature. After stirring for 1 hr at room temperature, methyl iodide (0.95 mL) was added dropwise and the mixture was stirred for 30 min. Ice water was added to the reaction solution and stirred; thereafter, the mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as colorless crystals (356 mg).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringstirred
  3. extractionthereafter, the mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-99ca2142c81e4693970d2970a01ba41e
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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