Potassium Carbonate → HCID 15458321, compound

HRID 1106979Notes

Reaction equation

HRID 1106979 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[S:11])[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:35])[CH2:33][S:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)=[CH:30][CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 525282176076-27-2HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 15458321HCID 15458321, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Quinoline-4(1H)-thione (3.50 g, 21.9 mmol) and potassium carbonate (3.95 g, 28.5 mmol) were suspended in dry acetone(350 ml). 1-Benzyloxy-4-bromoacetylbenzene (8.00 g, 26.3 mmol) was gradually added to the suspension under ice cooling and stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was added with water, 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 column chromatography (n-hexane:ethyl acetate=1:4) and recrystallized from ethyl acetate to obtain 5.43 g of the titled compound (64.4%) as yellow-white crystal.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was added with water
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was chromatographed by silica gel column chromatography (n-hexane:ethyl acetate=1:4)
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8ad58001efd04410b5969cf4ef5d3b17
Source dataset
uspto-grants-2000_05
Patent number
US06057447

Reaction notes

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