4-{2-(4-Hexylphenyl)thiazole-5-yl}phenol → HCID 23354802, compound

HRID 326513Notes

Reaction equation

HRID 326513 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])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>N1C=CC=CC=1.C(Cl)(=O)CCCC>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:21](=[O:24])[CH2:20][CH2:19][CH2:18][CH3:15])=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 233547624-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

Product 1

HCID 23354802HCID 23354802, compoundYield 170.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 61186Valeryl chlorideSolvent

Procedure

To a solution of 0.60 g (1.78 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)thiazole in 10 ml of pyridine, 0.36 ml (3.03 mM) of pentanoyl chloride was added on an ice water bath under stirring, followed by further stirring for 2 hours at room temperature. After the reaction, the reaction mixture was poured into 100 ml of ice water to precipitate a crystal. The crystal was recovered by filtration and dissolved in toluene, 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 of toluene-methanol to obtain 0.64 g of 2-(4-hexylphenyl)-5-(4-pentanoyloxyphenyl)thiazole (Yield: 85.4%). ##STR38##

Workup

  1. stirringby further stirring for 2 hours at room temperature
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. dissolutiondissolved in toluene
  6. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  8. customrecrystallized from a mixture solvent of toluene-methanol

Sources & evidence

ORD record
ord-869afd03a6504714ac8d1db74843067e
Source dataset
uspto-grants-1993_12
Patent number
US05269964

Reaction notes

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