Dimethylformamide → HCID 22320437, compound

HRID 433193Notes

Reaction equation

HRID 433193 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:9]1[N:10]([CH2:23][CH2:24]O)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:21])[C:12]=2[N:22]=1)[CH2:6][CH2:7][CH3:8].CN(C)C=O>C1(C)C=CC=CC=1>[CH2:5]([C:9]1[N:10]([CH2:23][CH2:24][Cl:3])[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:21])[C:12]=2[N:22]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22320509HCID 22320509, compound

Product 1

HCID 22320437HCID 22320437, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (3.8 g, 32 mmol) was added to a solution of 2-butyl-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.7 g, 13 mmol) in toluene containing a catalytic amount of N,N-dimethylformamide. The reaction mixture was heated to reflux and then capped. When analysis by high performance liquid chromatography indicated that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in warm methanol and then combined with concentrated ammonium hydroxide (5 mL). The mixture was chilled. The resulting precipitate was isolated by filtration, washed with cold methanol and then dried under vacuum overnight to provide 3.01 g of 2-butyl-1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a brown solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customcapped
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in warm methanol
  6. temperatureThe mixture was chilled
  7. customThe resulting precipitate was isolated by filtration
  8. washwashed with cold methanol
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-cef76cc2659e40fe93144e0c210e6866
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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