Thionyl Chloride → HCID 86633738, compound

HRID 415524Notes

Reaction equation

HRID 415524 reaction equation
[NH2:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18]O)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([Cl:14])[C:5]=2[N:15]=1.S(Cl)([Cl:22])=O>ClCCCl>[Cl:14][C:6]1[C:5]2[N:15]=[C:2]([NH2:1])[N:3]([CH2:16][CH2:17][CH2:18][Cl:22])[C:4]=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 86633739HCID 86633739, compound

Product 1

HCID 86633738HCID 86633738, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a round-bottomed flask containing 3-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol (7.17 g, 25.9 mmol) was added 1,2-dichloroethane (210 mL) and the suspension was stirred for 5 minutes. To the stirred suspension was added thionyl chloride (5.6 mL, 77.7 mmol) and the reaction was heated to 50° C. overnight. The reaction was cooled to ambient temperature, filtered, and the residue was washed with 1,2-dichloroethane (100 mL) and diethyl ether (3×100 mL) to afford the product. The product was dried under reduced pressure to afford 4-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-amine (7.92 g) as a light brown solid.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationfiltered
  3. washthe residue was washed with 1,2-dichloroethane (100 mL) and diethyl ether (3×100 mL)
  4. customto afford the product
  5. customThe product was dried under reduced pressure

Sources & evidence

ORD record
ord-a56ec57fdd6a413780b883dd28189688
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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