Tetrahydrofuran → 2-Hexyl-5-(6-decyloxynaphthalene-2-yl)-1,3,4-thiadiazole

HRID 1534758Notes

Reaction equation

HRID 1534758 reaction equation
[C:1]([NH:9][NH:10][C:11]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:19]=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.O1CCCC1.[OH-].[Na+]>O>[CH2:2]([C:1]1[S:43][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:19]=3)[CH:14]=2)=[N:10][N:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 87949Lawesson's reagentHCID 19907932N-heptanoyl-N'-(6-decyloxy-2-naphthoyl)hydrazine

Product 1

HCID 199079312-Hexyl-5-(6-decyloxynaphthalene-2-yl)-1,3,4-thiadiazoleYield 45.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 ml-round-bottomed flask, 1.20 g (2.64 mM) of N-heptanoyl-N'-(6-decyloxy-2-naphthoyl)-hydrazine, 1.20 g (2.97 mM) of Lawesson's reagent and 15 ml of tetrahydrofuran were placed, followed by refluxing for 45 minutes under stirring. After the reaction, the reaction mixture was poured into a solution of 0.95 g of sodium hydroxide in 100 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and purified by silica gel column chromatography (eluent: toluene). The resultant crystal was recrystallized from a mixture solvent (toluene-methanol) two times and further recrystallized from ethyl acetate and from toluene each once to obtain 0.54 g of 2-hexyl-5-(6-decyloxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 45.2%). ##STR29##

Workup

  1. temperatureby refluxing for 45 minutes
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washby washing with water
  6. custompurified by silica gel column chromatography (eluent: toluene)
  7. customThe resultant crystal was recrystallized from a mixture solvent (toluene-methanol) two times
  8. customfurther recrystallized from ethyl acetate and from toluene each once

Sources & evidence

ORD record
ord-498155d5bf164b34be486f1fb67b5e89
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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