1-Iodohexane → HCID 23354763, compound

HRID 234573Notes

Reaction equation

HRID 234573 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:28](I)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(O)CCC>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:20]([F:25])[CH:19]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 23354794HCID 23354794, compound

Product 1

HCID 23354763HCID 23354763, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a 30 ml-round-bottomed flask, 1.07 g (3.01 mM) of 2-(4-hexylphenyl)-5-(3-fluoro-4-hydroxyphenyl)thiazole prepared in Example 29, 0.23 g (3.48 mM) of potassium hydroxide and 5 ml of butanol were placed and heated. To the solution, 0.74 g (3.49 mM) of hexyl iodide was gradually added under heat-stirring, followed by heat-stirring for 5 hours about 90° C. After the reaction, the solvent was removed from the reaction mixture and water was added to the resultant residue to precipitate a crystal. The crystal was recovered by filtration and washed with water. The resultant crystal was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent of toluene-methanol to obtain 0.90 g of 2-(4-hexylphenyl)-5-(3-fluoro-4-hexyloxyphenyl)thiazole (Yield: 68.0%). ##STR205##

Workup

  1. temperatureheated
  2. stirringby heat-stirring for 5 hours about 90° C
  3. customAfter the reaction
  4. customthe solvent was removed from the reaction mixture and water
  5. additionwas added to the resultant residue
  6. customto precipitate a crystal
  7. filtrationThe crystal was recovered by filtration
  8. washwashed with water
  9. customThe resultant crystal was purified by silica gel column chromatography (eluent: toluene)
  10. customrecrystallized from a mixture solvent of toluene-methanol

Sources & evidence

ORD record
ord-9d9a17c1d9c14638bb72fd5b9b7322e8
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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