Chloride → HCID 57756431, compound

HRID 228573Notes

Reaction equation

HRID 228573 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]([CH3:22])=[CH:18][C:17]=1[CH:23]([OH:28])[CH2:24][CH2:25][CH2:26][CH3:27].C1CCN2C(=NCCC2)CC1.[Cl-].O>C(Cl)Cl>[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]([CH3:22])=[CH:18][C:17]=1[C:23](=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57756523HCID 57756523, compound2×

Product 1

HCID 57756431HCID 57756431, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1-{2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-1-pentanol (compound 10) (45.7 mg) was dissolved in methylene chloride (2 ml) to prepare a solution. 1,8-Diazabicyclo[5.4.0]-7-undecene (37 mg) was then added to the solution, and the mixture was cooled to 0° C. N-Tert-butylbenzenesulfineimidoyl chloride (43 mg) was dissolved in methylene chloride to prepare a solution, the solution was added thereto, and the mixture was stirred at 0° C. for 40 min. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (27.6 mg, yield 61%).

Workup

  1. customto prepare a solution
  2. customto prepare a solution
  3. additionthe solution was added
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was then washed with saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-f71b5824feaf48d5a8049ee3344e5775
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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