Water → HCID 18790526, compound

HRID 1106982Notes

Reaction equation

HRID 1106982 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][S:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:4]([O:22][CH3:23])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O>CN(C=O)C>[CH3:23][O:22][C:4]1[CH:3]=[C:2]([O:1][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:7]=[CH:6][C:5]=1[C:8](=[O:21])[CH2:9][S:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 18790532HCID 18790532, compound2×

Product 1

HCID 18790526HCID 18790526, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(4-Hydroxy-2-methoxyphenyl)-2-oxoethylthio]-quinoline (Compound 12; 83 mg, 0.25 mmol) and potassium carbonate(42 mg, 0.25 mmol) were suspended in dry DMF (2.0 ml). Hexylbromide (0.041 ml, 0.28 mmol) was addded at -15° C. to the suspension and stirred at room temperature overnight. The reaction mixture was added with water under ice cooling, extracted with ethyl acetate, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed by silica gel chromatography (n-hexane:ethyl acetate=1:4) to obtain 82.1 mg of the titled compound (80.3%).

Workup

  1. customwas addded at -15° C. to the suspension
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was chromatographed by silica gel chromatography (n-hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-036d096359d54298989e64354f43ca44
Source dataset
uspto-grants-2000_05
Patent number
US06057447

Reaction notes

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