Dimethyl Sulfoxide → HCID 22667082, compound

HRID 1375762Notes

Reaction equation

HRID 1375762 reaction equation
[H-].[Na+].CS(C)=O.[NH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[C:10]([CH3:16])[CH:9]=1.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([O:15][C:11]3[C:10]([CH3:16])=[CH:9][C:8]([NH2:7])=[C:13]([CH3:14])[CH:12]=3)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 22667082HCID 22667082, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60 wt %, 1.17 g) was added to dimethyl sulfoxide (25 ml), and the mixture was stirred at 60° C. for 30 min and was then cooled to room temperature. Next, 4-amino-2,5-dimethylphenol (4.00 g) was added thereto, and the mixture was stirred at room temperature for 10 min. 7-(Benzyloxy)-4-chloro-6-methoxyquinoline (4.36 g) was then added thereto. The mixture was stirred for 22 hr before water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and methanol was added to the residue to prepare a suspension. The precipitated crystal was collected by suction filtration to give 3.04 g (yield 52%) of the title compound.

Workup

  1. temperaturewas then cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 10 min
  3. additionwas added to the reaction solution
  4. extractionfollowed by extraction with chloroform
  5. washThe chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure, and methanol
  8. additionwas added to the residue
  9. customto prepare a suspension
  10. filtrationThe precipitated crystal was collected by suction filtration

Sources & evidence

ORD record
ord-d43c33b7b5dc401cbc62c0e8a240a37c
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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