4-Toluenesulfonyl chloride → HCID 59026676, compound

HRID 606130Notes

Reaction equation

HRID 606130 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([C:16]1[O:20][N:19]=[C:18]([CH2:21][N:22]2[C:34]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[N:27]=[CH:26][C:25]=3[N:24]=[CH:23]2)[CH:17]=1)[CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:47].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([C:16]1[O:20][N:19]=[C:18]([CH2:21][N:22]2[C:34]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[N:27]=[C:26]([NH2:47])[C:25]=3[N:24]=[CH:23]2)[CH:17]=1)[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67041325HCID 67041325, compound

Product 1

HCID 59026676HCID 59026676, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (930 mg of 77% pure material, 4.2 mmol) was added to a solution of 1-[(5-butylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinoline (1.06 g, 3.46 mmol) in chloroform (40 mL), and the solution was stirred for 1.5 hours at room temperature. p-Toluenesulfonyl chloride (726 g, 3.81 mmol) and concentrated ammonium hydroxide (15 mL) were then added, and the mixture was stirred vigorously for three hours at room temperature. Saturated aqueous sodium bicarbonate was added, and the aqueous layer was separated and extracted several times with chloroform. The combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange solid was purified by flash column chromatography on silica gel (eluting with 4% to 8% methanol in dichloromethane) to provide 0.92 g of 1-[(5-butylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as a tan crystalline solid, mp 201-203° C.

Workup

  1. stirringthe mixture was stirred vigorously for three hours at room temperature
  2. customthe aqueous layer was separated
  3. extractionextracted several times with chloroform
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting orange solid was purified by flash column chromatography on silica gel (eluting with 4% to 8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f7d57908d36143d3b6f6254608502141
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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