3-Chlorobenzoic Acid → HCID 10109850, compound

HRID 897192Notes

Reaction equation

HRID 897192 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][CH3:25])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:34])C=1.ClC1C=C(C=CC=1)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24]([CH3:25])=[O:34])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 10269675HCID 10269675, compound

Product 1

HCID 10109850HCID 10109850, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, 2-butyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 2.80 mmol) and chloroform (14 mL). Solid 3-chloroperbenzoic acid (0.69 g, 3.09 mmol) was added portion wise over 5 minutes and the reaction was stirred at ambient temperature for 20 minutes at which time the starting material was completely consumed. The solution was partitioned between chloroform and saturated aqueous sodium bicarbonate. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford an off-white solid which was shown by 1H-NMR to be the 3-chlorobenzoic acid salt of the desired product. The solid was stirred in water and then made basic (pH 10) by addition of solid sodium carbonate. The resulting free base was collected by filtration to provide a white solid which was recrystallized from acetonitrile to give 2-butyl-1-[5-(methylsulfinyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.40 g, 1.07 mmol) as a white powder, m.p. 119-121° C.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customwas completely consumed
  3. customThe solution was partitioned between chloroform and saturated aqueous sodium bicarbonate
  4. customThe layers were separated
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford an off-white solid which

Sources & evidence

ORD record
ord-caaa095bc39f43e6b7492c4bfd4ee52b
Source dataset
uspto-grants-2005_07
Patent number
US06921826B2

Reaction notes

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