Chloroacetyl chloride → HCID 67157353, compound

HRID 549122Notes

Reaction equation

HRID 549122 reaction equation
[Cl:1][CH2:2][C:3](Cl)=O.[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:18][CH:19]([CH3:30])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[C:12]([NH2:17])[CH:13]=[N:14]2)=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:18]([CH:19]([CH3:30])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:3]([CH2:2][Cl:1])=[N:17][C:12]=3[CH:13]=[N:14][C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 69105781HCID 69105781, compound

Product 1

HCID 67157353HCID 67157353, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of chloroacetyl chloride (16.1 g, 142 mmol) in chloroform (120 mL) was added dropwise to a solution of 7-bromo-N4-[3-(tert-butyldimethylsilanyloxy)-1-methylpropyl]quinoline-3,4-diamine (54.96 g, 129.5 mmol) in chloroform (500 mL), and the reaction was stirred for three days at room temperature. The solvent was removed under reduced pressure, and the intermediate amide was heated at reflux for two hours in glacial acetic acid (600 mL). The acetic acid was removed under reduced pressure, and the residue was passed through a plug of silica gel (eluting with dichloromethane) to provide 9.53 g of 7-bromo-1-[3-(tert-butyldimethylsilanyloxy)-1-methylpropyl]-2-chloromethyl-1H-imidazo[4,5-c]quinoline and a mixture of three other products. The mixture of products was dissolved in glacial acetic acid and heated at reflux for two days. The acetic acid was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with 0% to 5% 2 M methanolic ammonia in dichloromethane) to provide 9.14 g of 3-{2-[(acetyloxy)methyl]-7-bromo-1H-imidazo[4,5-c]quinolin-1-yl}butyl acetate.

Workup

  1. customThe solvent was removed under reduced pressure
  2. temperaturethe intermediate amide was heated
  3. temperatureat reflux for two hours in glacial acetic acid (600 mL)
  4. customThe acetic acid was removed under reduced pressure

Sources & evidence

ORD record
ord-f02d2a9973d740baad30e8149b33b168
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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