Water → HCID 23022717, compound

HRID 1727868Notes

Reaction equation

HRID 1727868 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH2:25])=[S:24])=[CH:18][CH:17]=1.C(N(CC)CC)C.Br[CH:34]([CH3:38])[C:35](=O)[CH3:36].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[S:24][C:34]([CH3:38])=[C:35]([CH3:36])[N:25]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 131422-Butanone, 3-bromo-HCID 85824834HCID 85824834, compound

Product 1

HCID 23022717HCID 23022717, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}thiourea (50 mg) was dissolved in dimethylformamide (5 ml) to prepare a solution. Triethylamine (43 mg) and 3-bromo-2-butanone (43 mg) were added to the solution, and the mixture was stirred at room temperature for 3 hr. Water and ethyl acetate were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was then washed with saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The crude thus obtained was purified by column chromatography on silica gel using chloroform/methanol for development to give the title compound (42 mg, yield 73%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under the reduced pressure
  6. customThe crude thus obtained
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d93b8e625e66444fb17b851abd439eee
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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