4-Toluenesulfonyl chloride → HCID 58833643, compound

HRID 540869Notes

Reaction equation

HRID 540869 reaction equation
[CH:1]([NH:4][C:5](=[O:27])[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:19]([CH2:20][CH2:21][CH3:22])[C:18]([CH2:23][CH2:24][O:25][CH3:26])=[N:17][C:12]=3[CH:13]=[N:14][C:15]=2[CH:16]=1)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:51]>C(Cl)(Cl)Cl>[CH:1]([NH:4][C:5](=[O:27])[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:19]([CH2:20][CH2:21][CH3:22])[C:18]([CH2:23][CH2:24][O:25][CH3:26])=[N:17][C:12]=3[C:13]([NH2:51])=[N:14][C:15]=2[CH:16]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 68971459HCID 68971459, compound

Product 1

HCID 58833643HCID 58833643, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2-Methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl isopropylcarbamate (1.89 g, 5.10 mmol) was dissolved in chloroform (41 mL). 3-Chloroperoxybenzoic acid (60% pure, 1.60 g, 5.56 mmol) was added in one portion. After 30 minutes the golden solution was diluted with ammonium hydroxide (41 mL), and p-toluenesulfonyl chloride (0.927 g, 4.86 mmol) was added. The reaction was stirred for 1.5 hours. The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined, washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The solid residue was recrystallized from acetonitrile to provide 0.986 g of 4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl isopropylcarbamate as a granular, peach-colored solid, mp 144.0-146.0° C.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous fraction was extracted with dichloromethane
  4. washwashed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-f31747b4681c4543aa09d2a4961eedbb
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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