Thionyl Chloride → HCID 22320497, compound

HRID 497903Notes

Reaction equation

HRID 497903 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:18])[N:14]([CH2:15][CH2:16]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:21])=O>ClCCCl>[Cl:21][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH3:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22320558HCID 22320558, compound

Product 1

HCID 22320497HCID 22320497, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Using the general method of Example 6 Part A except that a solvent (55 mL of 1,2-dichloroethane) was included, 2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (4.0 g, 16.51 mol) was chlorinated using thionyl chloride (2.41 mL, 33.02 mmol) to provide 3.9 g of 1-(2-chloroethyl)-2-methyl-1H-imidazo[4,5-c]quinoline-4-amine as a fine, white powder.

Sources & evidence

ORD record
ord-5a2a51186aff4f3ea5500337dd8d628d
Source dataset
uspto-grants-2005_09
Patent number
US06949649B2

Reaction notes

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