Sodium methanethiolate → HCID 69081425, compound

HRID 244818Notes

Reaction equation

HRID 244818 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:13]([CH2:20][O:21][CH2:22][CH3:23])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[CH3:24][S-:25].[Na+]>CN(C)C=O>[CH2:22]([O:21][CH2:20][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([S:25][CH3:24])=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:12]=1)[CH3:23]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 21984215HCID 21984215, compound

Product 1

HCID 69081425HCID 69081425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinoline (U.S. Patent Application Publication No. US 2004/0147543 Examples 163-175, 1.0 g, 2.64 mmol) and sodium thiomethoxide (0.185 g, 2.64 mmol) were dissolved in N,N-dimethylformamide (25 mL). The reaction mixture was stirred at ambient temperature for 20 minutes and then heated at 55° C. for 16 hours. The reaction was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and sequentially washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. 2-Ethoxymethyl-1-(3-methoxypropyl)-7-methylthio-1H-imidazo[4,5-c]quinoline was isolated as 1.1 g of a pale yellow oil.

Workup

  1. temperatureheated at 55° C. for 16 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washsequentially washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-029d524923e6476f87ed1e0fd29b882a
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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