Water → 2-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinoline

HRID 497904

Reaction equation

HRID 497904 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH3:22].O>CN(C)C=O>[CH3:22][C:10]1[N:9]([CH2:8][CH2:7][CH2:6][CH2:5][S:2][CH3:1])[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 223204561-(4-chlorobutyl)-2-methyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 223204892-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinolineYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (2.02 g of 95%, 27.40 mmol) was added in a single portion to a solution of 1-(4-chlorobutyl)-2-methyl-1H-imidazo[4,5-c]quinoline (5.0 g, 18.26 mmol) in anhydrous N,N-dimethylformamide (91 mL). After 30 minutes the reaction mixture was poured with rapid stirring into water (500 mL). The resulting solution was extracted with chloroform (2×200 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) then with brine (100 mL), dried over sodium sulfate, filtered and then concentrated under reduced pressure to provide 5.0 g 2-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinoline as a light yellow oil.

Workup

  1. additionAfter 30 minutes the reaction mixture was poured
  2. extractionThe resulting solution was extracted with chloroform (2×200 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (100 mL)
  4. dry with materialwith brine (100 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7f40a447a12452fb522564500af04a2
Source dataset
uspto-grants-2005_09
Patent number
US06949649B2

Linked notes

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