Thionyl Chloride → HCID 22381773, compound

HRID 895783Notes

Reaction equation

HRID 895783 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:22][O:23][CH2:24][CH3:25])[N:18]([CH2:19][CH2:20]O)[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.CO.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[ClH:3].[Cl:3][CH2:20][CH2:19][N:18]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=[C:17]1[CH2:22][O:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13007357HCID 13007357, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 22381773HCID 22381773, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (5 mL) and 4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline1-ethanol (1 g) were combined and heated on a steam bath until thin layer chromatography (20% methanol/ethyl acetate) showed the disappearance of starting material. The reaction mixture was cooled to ambient temperature and then slowly poured into a mixture of ice and water. The mixture was neutralized with sodium bicarbonate and then extracted 3 times with dichloromethane. The extracts were combined, washed 3 times with aqueous sodium bicarbonate, dried with magnesium sulfate, filtered and then concentrated under vacuum. Acetone (about 10 mL) was added to the residue followed by methanolic hydrogen chloride (about 1 mL). The mixture was refluxed and a precipitate formed. The reaction mixture was cooled to ambient temperature. The precipitate was isolated by filtration and then washed with acetone. The solid was dissolved in hot methanol and then precipitated by the addition of acetone. The precipitate was isolated by filtration, washed with water and then dried to provide 1-(2-chloroethyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride. Analysis:

Workup

  1. extractionextracted 3 times with dichloromethane
  2. washwashed 3 times with aqueous sodium bicarbonate
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionAcetone (about 10 mL) was added to the residue
  7. temperatureThe mixture was refluxed
  8. customa precipitate formed
  9. temperatureThe reaction mixture was cooled to ambient temperature
  10. customThe precipitate was isolated by filtration
  11. washwashed with acetone
  12. dissolutionThe solid was dissolved in hot methanol
  13. customprecipitated by the addition of acetone
  14. customThe precipitate was isolated by filtration
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-4ed2f667d2fb45b2ae55f6405ed30b7a
Source dataset
uspto-grants-2005_07
Patent number
US06916925B1

Reaction notes

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