Benzyltrimethylammonium hydroxide → 2-Octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorenone

HRID 249219Notes

Reaction equation

HRID 249219 reaction equation
[CH2:1]([C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([C:22]4[S:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:25][N:26]=4)=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-:33].C[N+](C)(C)CC1C=CC=CC=1>N1C=CC=CC=1>[CH2:1]([C:9]1[C:10](=[O:33])[C:11]2[C:19](=[CH:20][CH:21]=1)[C:18]1[C:13](=[CH:14][C:15]([C:22]3[S:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:25][N:26]=3)=[CH:16][CH:17]=1)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 197606622-Octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorene

Product 1

HCID 678859042-Octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorenoneYield 53.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.20 g (0.45 mM) of 2-octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorene in 20 ml of pyridine, 0.27 ml of 40%-trimethylbenzylammonium hydroxide aqueous solutions as added at 3.5°-4.5° C. under stirring on ice water bath, followed by stirring for 0.5 hour at 3.5°-4.5° C. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in toluene, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1) and recrystallized from a mixture solvent of toluene-acetone to obtain 0.11 g of 2-octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorenone (Yield: 53.3%). ##STR89##

Workup

  1. stirringby stirring for 0.5 hour at 3.5°-4.5° C
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with water
  6. dissolutiondissolved in toluene
  7. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent under reduced pressure
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1)
  10. customrecrystallized from a mixture solvent of toluene-acetone

Sources & evidence

ORD record
ord-f43a152c0c8f49e49bf27c325b8742da
Source dataset
uspto-grants-1993_05
Patent number
US05213709

Reaction notes

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