Water → HCID 15027124, compound

HRID 326515Notes

Reaction equation

HRID 326515 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].[CH2:29](I)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:25]=3)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 15027123HCID 15027123, compound

Product 1

HCID 15027124HCID 15027124, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.40 g (1.10 mM) of 2-(4-octylphenyl)-5-(4-hydroxyphenyl)thiazole in 20 ml of N,N-dimethylformamide (DMF), 0.40 g (1.10 mM) of potassium hydroxide was added, followed by stirring for 45 minutes at 100° C. To the mixture, 0.36 g (1.70 mM) of hexyl iodide was added at 100° C. under stirring, followed by further stirring for 6 hours and 16 minutes at 120° C. After the reaction, the reaction mixture was poured into 100 ml of water and extracted with ethyl acetate. The organic layer was washed with water, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from ethanol to obtain 0.16 g of 2-(4-octylphenyl)-5-(4-hexyloxyphenyl)thiazole (Yield: 32.3%). ##STR43##

Workup

  1. stirringunder stirring
  2. stirringby further stirring for 6 hours and 16 minutes at 120° C
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5e2af2e411994d0b8e543ffa5afba457
Source dataset
uspto-grants-1993_12
Patent number
US05269964

Reaction notes

Loading…