1-Iodohexane → 2-Hexyl-5-(6-hexyloxynaphthalene-2-yl)-1,3,4-thiadiazole

HRID 1534769Notes

Reaction equation

HRID 1534769 reaction equation
[CH2:1]([C:7]1[S:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=3)[CH:13]=2)=[N:10][N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:25](I)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(O)CCC>[CH2:1]([C:7]1[S:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:18]=3)[CH:13]=2)=[N:10][N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 1360772002-Hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole

Product 1

HCID 199079372-Hexyl-5-(6-hexyloxynaphthalene-2-yl)-1,3,4-thiadiazoleYield 35.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

In a 50 ml-round-bottomed flask, 0.60 g (1.92 mM) of 2-hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole prepared in Step ii) of Example 24, 0.18 g (2.73 mM) of potassium hydroxide and 15 ml of butanol were placed and dissolved under heating. To the mixture, 0.53 g (2.50 mM) of hexyl iodide was added at about 100° C. under stirring, followed by refluxing for 6 hours under stirring. After the reaction, butanol was distilled off under reduced pressure, and water and ethyl acetate were added to the residue, followed by stirring. The resultant organic layer was washed with water, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent to obtain a solid. The solid was purified by silica gel column chromatography (eluent: benzene) and recrystallized from a mixture solvent (ethyl acetate-ethanol) to obtain 0.27 g of 2-hexyl-5-(6-hexyloxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 35.5 %). ##STR141##

Workup

  1. dissolutiondissolved
  2. temperatureunder heating
  3. temperatureby refluxing for 6 hours
  4. stirringunder stirring
  5. distillationwas distilled off under reduced pressure, and water and ethyl acetate
  6. additionwere added to the residue
  7. stirringby stirring
  8. washThe resultant organic layer was washed with water
  9. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
  10. customto obtain a solid
  11. customThe solid was purified by silica gel column chromatography (eluent: benzene)
  12. customrecrystallized from a mixture solvent (ethyl acetate-ethanol)

Sources & evidence

ORD record
ord-0c6d938b28d647d5afb80bb009c4b55b
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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