Thionyl Chloride → HCID 178508169, compound

HRID 388617Notes

Reaction equation

HRID 388617 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([OH:24])[N:18]([CH2:19][CH2:20][CH2:21][CH2:22]O)[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>ClCCCl>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([OH:24])[N:18]([CH2:19][CH2:20][CH2:21][CH2:22][Cl:3])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178508170HCID 178508170, compound

Product 1

HCID 178508169HCID 178508169, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (1.1 mL, 15 mmol) was added to a solution of 4-amino-1-(4-hydroxybutyl)-1H-imidazo[4,5-c]quinolin-2-ol (3.5 g, 13 mmol) in 1,2-dichloroethane (60 mL), and the reaction was stirred at 50° C. overnight. A solid was present, which was collected by filtration and washed with diethyl ether (500 to 600 mL) to provide 3.24 g of 4-amino-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-2-ol as a light gray solid.

Workup

  1. filtrationwhich was collected by filtration
  2. washwashed with diethyl ether (500 to 600 mL)

Sources & evidence

ORD record
ord-7ed98ceceae343b9ae3316eb44a657af
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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