Thiophenol → 1-{2-[3-(phenylthio)propoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 547299Notes

Reaction equation

HRID 547299 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Cl[CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([NH2:32])[C:22]=2[N:21]=[C:20]1[CH2:33][CH2:34][CH3:35]>CN(C=O)C>[C:1]1([S:7][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][N:19]2[C:31]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N:24]=[C:23]([NH2:32])[C:22]=3[N:21]=[C:20]2[CH2:33][CH2:34][CH3:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 67203500HCID 67203500, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 672030091-{2-[3-(phenylthio)propoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere thiophenol (0.9 mL, 8.6 mmol) was added to a suspension of sodium hydride (0.19 g, 7.9 mmol) in DMF (25 mL). After hydrogen evolution had ceased, 1-[2-(3-chloropropoxy)ethyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.50 g, 7.2 mmol, prepared by the methods of Parts A-I) was added. The reaction mixture was stirred at ambient temperature for 1.5 hours at which time analysis by HPLC indicated that all of the starting material had been consumed. The reaction mixture was poured into water (250 mL) with rapid stirring. Sodium carbonated (˜0.5 g) was added to neutralize any excess thiolate and the pH was adjusted to ˜14 with 50% sodium hydroxide. The resulting tan precipitate was isolated by filtration and then recrystallized from acetonitrile to provide 1.95 g of 1-{2-[3-(phenylthio)propoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a tan crystalline solid.

Workup

  1. additionwas added
  2. customhad been consumed
  3. additionThe reaction mixture was poured into water (250 mL) with rapid stirring
  4. additionwas added
  5. customThe resulting tan precipitate was isolated by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-20681a8f45c940cabfe302bb196d1516
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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