Chloride → HCID 13295785, compound

HRID 1709839Notes

Reaction equation

HRID 1709839 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][CH2:14]O)[CH:4]=[CH:3][CH:2]=1.[Cl-:16].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[Cl:16][CH2:14][CH2:13][CH2:12][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

5

Reactant 3

HCID 312ChlorideHCID 11430Potassium CarbonateHCID 132957843-(8-Quinolinyloxy)-1-propanol

Product 1

HCID 13295785HCID 13295785, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-(8-quinolinyloxy)-1-propanol (32.0 g, 0.158 mole) and thinoyl chloride (24.0 g, 0.203 mole) was heated at reflux for 5 hours in 300 ml of dry benzene (dried over 4A molecular sieves). The reaction mixture was cooled to room temperature and then stripped to dryness. The residue was treated with potassium carbonate solution (30 g in 500 ml of water). The gummy residue was dissolved in chlorofrom and extracted with the potassium carbonate solution. The chloroform layer was dried over anhydrous sodium sulfate, filtered, and solvent removed to give a dark mass which crystallized. The mass was treated with 500 ml of boiling hexane. The hexane layer was decanted off from insoluble oil. A white solid crystallized on cooling, and was collected by filtration. The solid was dried in vacuo at room temperature overnight to give 26.69 g (76.2%) of white, crystalline solid, m.p. 69°-71° C.

Workup

  1. dissolutionThe gummy residue was dissolved in chlorofrom
  2. extractionextracted with the potassium carbonate solution
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customsolvent removed
  6. customto give a dark mass which
  7. customcrystallized
  8. additionThe mass was treated with 500 ml of boiling hexane
  9. customThe hexane layer was decanted off from insoluble oil
  10. customA white solid crystallized
  11. temperatureon cooling
  12. filtrationwas collected by filtration
  13. customThe solid was dried in vacuo at room temperature overnight
  14. customto give 26.69 g (76.2%) of white, crystalline solid, m.p. 69°-71° C.

Sources & evidence

ORD record
ord-3200c642bd0b47f39d3a9a83b1c3845e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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