1-Butanol → HCID 19770588, compound

HRID 1589722Notes

Reaction equation

HRID 1589722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:15]=3)=[N:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:26](I)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[OH-].[K+].C(O)CCC>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:15]=3)=[N:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 135760568HCID 135760568, compound

Product 1

HCID 19770588HCID 19770588, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.30 g (0.84 mM) of 2-(3-fluoro-4-hydroxyphenyl)-5-(4-hexylphenyl)-1,3,4-thiadiazole, 0.23 g (1.09 mM) of hexyl iodide, 0.08 g of 85%-potassium hydroxide and 6 ml of butanol were mixed, followed by refluxing for 5 hours under stirring. After the reaction, 10 ml of methanol was added to the reaction mixture, followed by cooling to room temperature and further cooling in a freezer 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 magnesium sulfate. The magnesium sulfate was recovered by filtration and the filtrate was condensed into a solid. The solid was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (ethanol/hexane) to obtain 0.13 g of 2-(3-fluoro-4-hexyloxyphenyl)-5-(4-hexylphenyl)-1,3,4-thiadiazole (Yield: 35.1%). ##STR23##

Workup

  1. temperatureby refluxing for 5 hours
  2. additionwas added to the reaction mixture
  3. temperaturefurther cooling in a freezer
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washwashed with methanol
  7. dissolutionThe resultant crystal was dissolved in toluene
  8. washwashed with water
  9. dry with materialby drying with anhydrous magnesium sulfate
  10. filtrationThe magnesium sulfate was recovered by filtration
  11. customcondensed into a solid
  12. customThe solid was purified by silica gel column chromatography (eluent: toluene)
  13. customrecrystallized from a mixture solvent (ethanol/hexane)

Sources & evidence

ORD record
ord-8e9bac86de7c42689ca1bf63e7951206
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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