Butyl bromide → HCID 19907929, compound

HRID 1534763Notes

Reaction equation

HRID 1534763 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([OH:28])[CH:24]=4)[CH:19]=3)=[N:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:31](Br)[CH2:32][CH2:33][CH3:34]>C(O)CCC>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH2:31][CH2:32][CH2:33][CH3:34])[CH:24]=4)[CH:19]=3)=[N:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 136058235HCID 136058235, compound

Product 1

HCID 19907929HCID 19907929, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a 20 ml-round-bottomed flask, 0.30 g (0.77 mM) of 2-(4-hexylphenyl)-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole, 0.08 g (1.21 mM) of potassium hydroxide was 4 ml of n-butanol were placed and dissolved at about 80° C. To the mixture, 0.12 ml (1.12 mM) of n-butyl bromide was added at 80° C. under stirring, followed by refluxing for 4 hours and 10 minutes under stirring. After the reaction, the reaction mixture was cooled on an iced water bath to precipitate a crystal. The crystal was recovered by filtration and washed with methanol. The resultant crystal was dissolved in toluene and washed with water, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene-methanol) to obtain 0.25 g of 2-(4-hexylphenyl)-5(6-butoxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 72.8%) ##STR36##

Workup

  1. dissolutiondissolved at about 80° C
  2. temperatureby refluxing for 4 hours and 10 minutes
  3. stirringunder stirring
  4. customAfter the reaction
  5. temperaturethe reaction mixture was cooled on an iced water bath
  6. customto precipitate a crystal
  7. filtrationThe crystal was recovered by filtration
  8. washwashed with methanol
  9. dissolutionThe resultant crystal was dissolved in toluene
  10. washwashed with water
  11. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
  12. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  13. customrecrystallized from a mixture solvent (toluene-methanol)

Sources & evidence

ORD record
ord-20f39c05040b4c9197b5b5a4195b3c34
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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