Sodium Hydroxide → HCID 23354809, compound

HRID 234583Notes

Reaction equation

HRID 234583 reaction equation
O=[C:2]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:3][NH:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:13]=2)[CH:8]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1.[OH-].[Na+]>O1CCCC1>[CH2:18]([O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:5]1[S:43][C:2]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:3][N:4]=1)[CH:16]=[CH:15]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 87949Lawesson's reagentHCID 23354782HCID 23354782, compound

Product 1

HCID 23354809HCID 23354809, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 0.40 g (0.88 mM) of 2-oxooctyl-(6-decyloxy-2-naphthoyl)amine, 0.38 g (0.94 mM) of Lawesson's reagent and 6 ml of tetrahydrofuran were placed in a 30 ml-round-bottomed flask, followed by heat-refluxing for 45 minutes under stirring. After the reaction, the reaction mixture was poured into a solution of 0.27 g of sodium hydroxide in 70 ml of 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. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1) and recrystallized from a mixture solvent of acetonemethanol to obtain 0.21 g of 2-(6-decyloxy-2-naphthyl)-5-hexylthiazole (Yield: 52.7%). ##STR236##

Workup

  1. temperatureby heat-refluxing for 45 minutes
  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. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1)
  9. customrecrystallized from a mixture solvent of acetonemethanol

Sources & evidence

ORD record
ord-047a01c63ee84cc0a39837d7f79c1398
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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