4-Toluenesulfonyl chloride → HCID 10014577, compound

HRID 1373946Notes

Reaction equation

HRID 1373946 reaction equation
[N:1]1([NH:14][CH:15]([CH3:17])[CH3:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:30].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[CH:15]([NH:14][N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:30])[C:4]=2[N:3]=[CH:2]1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21075781HCID 21075781, compound

Product 1

HCID 10014577HCID 10014577, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of N-(1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (1.36 g, 5.66 mmol) in 50 mL of chloroform was cooled in a cold water bath. The solution was treated with MCPBA (2.03 g, 7.07 mmol) over 5 min and then allowed to warm to ambient temperature. After 1 h, TLC showed complete conversion to the intermediate 5-N-oxide. The reaction mixture was again cooled with a cold water bath. The solution was treated with concentrated ammonium hydroxide solution (25 mL, 30%) and stirred rapidly to homogenize. The reaction mixture was treated with p-toluenesulfonyl chloride (1.13 g, 5.94 g) over 5 min and allowed to warm to ambient temperature. After 30 min, the reaction mixture was diluted with 50 mL of CHCl3 and 25 mL of water. An undissolved solid between the phases was filtered off, saved, and the phases were separated. The organic portion was washed with saturated NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL). The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan/orange solid. A high-performance liquid chromatography (HPLC) analysis of the filtered solid matched that of the solid from the concentrated organic extracts. The combined solid was recrystallized twice from MeOH to give 1.18 g of N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine as an off-white solid.

Workup

  1. temperatureThe reaction mixture was again cooled with a cold water bath
  2. stirringto homogenize
  3. temperatureto warm to ambient temperature
  4. waitAfter 30 min
  5. filtrationAn undissolved solid between the phases was filtered off
  6. customthe phases were separated
  7. washThe organic portion was washed with saturated NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL)
  8. dry with materialThe organic portion was then dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto yield a tan/orange solid
  12. customThe combined solid was recrystallized twice from MeOH

Sources & evidence

ORD record
ord-86cafe5b86bf4b2c93c6c3a49ec425a6
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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