1-Iodohexane → HCID 23354763, compound

HRID 326517Notes

Reaction equation

HRID 326517 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[N:17]=[CH:16][C:15]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([F:33])[CH:27]=3)(C3C=CC(O)=C(F)C=3)[S:14]2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:36](I)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C(O)CCC>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[C:28]([F:33])[CH:27]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 67686570HCID 67686570, compound

Product 1

HCID 23354763HCID 23354763, compoundYield 89.5%

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)-5-(3-fluoro-4-hydroxyphenyl)thiazole prepared in Synthesis Example 7, 0.23 g (3.48 mM) of potassium hydroxide and 5 ml of butanol were placed and heated to provide a solution. To the solution, 0.74 g (3.49 mM) of hexyl iodide was gradually added under heat stirring, followed by stirring for 5 hours at about 90° C. After the reaction, the solvent in the reaction mixture was distilled off under reduced pressure and water was added to the 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 (toluene-methanol) to obtain 0.90 g of 2-(4-hexylphenyl)-5-(3-fluoro-4-hexyloxyphenyl)thiazole (Yield: 68.0%). ##STR51##

Workup

  1. temperatureheated
  2. customto provide a solution
  3. temperatureunder heat
  4. stirringby stirring for 5 hours at about 90° C
  5. customAfter the reaction
  6. distillationthe solvent in the reaction mixture was distilled off under reduced pressure and water
  7. additionwas added to the residue
  8. customto precipitate a crystal
  9. filtrationThe crystal was recovered by filtration
  10. washwashed with water
  11. customThe resultant crystal was purified by silica gel column chromatography (eluent: toluene)
  12. customrecrystallized from a mixture solvent (toluene-methanol)

Sources & evidence

ORD record
ord-a0cc9a062d554ca79f1efe73970dc756
Source dataset
uspto-grants-1993_12
Patent number
US05269964

Reaction notes

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