Sodium Hydroxide → 2-Octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorene

HRID 249218Notes

Reaction equation

HRID 249218 reaction equation
[C:1]([NH:9][NH:10][C:11]([C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][C:19]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1)=O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1.[OH-].[Na+]>O1CCCC1>[CH2:26]([C:19]1[CH:20]=[CH:21][C:22]2[C:23]3[C:15](=[CH:14][C:13]([C:11]4[S:43][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[N:9][N:10]=4)=[CH:25][CH:24]=3)[CH2:16][C:17]=2[CH:18]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 87949Lawesson's reagentHCID 19760658HCID 19760658, compound

Product 1

HCID 197606622-Octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluoreneYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 30 ml-round-bottomed flask, 0.65 g (1.45 mM) of N-heptanoyl-N'-(7-octyl-2-fluorenecarbonyl)hydrazine, 0.62 g (1.53 mM) of Lawesson's reagent and 10 ml of tetrahydrofuran were placed, followed by heat-refluxing for 1.5 hours. After the reaction, the reaction mixture was poured into a solution of 0.45 g of sodium hydroxide in 100 ml of ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in toluene, followed by washing with water, drying with anhydrous sodium sulfate and distilling-off of the solvent. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized two times from a mixture solvent of toluene-methanol to obtain 0.40 g of 2-octyl-7-(5-hexyl-1,3,4-thiadiazole-2-yl)fluorene (Yield: 61.8%). ##STR87##

Workup

  1. temperatureby heat-refluxing for 1.5 hours
  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. washby washing with water
  8. dry with materialdrying with anhydrous sodium sulfate and distilling-off of the solvent
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  10. customrecrystallized two times from a mixture solvent of toluene-methanol

Sources & evidence

ORD record
ord-8b8f0315f03a49b890bec5de92d94c45
Source dataset
uspto-grants-1993_05
Patent number
US05213709

Reaction notes

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