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

HRID 1534766Notes

Reaction equation

HRID 1534766 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][C:24](=[O:26])[CH3:25])[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:36])=CC=1.O1CCCC1.[OH-].[Na+]>O>[CH2:2]([C:1]1[S:36][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][C:24](=[O:26])[CH3:25])[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 19907933HCID 19907933, compound

Product 1

HCID 199079422-Hexyl-5-(6-acetoxynaphthalene-2-yl)-1,3,4-thiadiazoleYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 ml-round-bottomed flask, 3.00 g (8.42 mM) of N-heptanoyl-N'-(6-acetoxy-2-naphthoyl)hydrazine, 3.83 g (9.47 mM) of Lawesson's reagent and 40 ml of tetrahydrofuran were placed, followed by refluxing for 1 hour under stirring. After the reaction, the reaction mixture was cooled on an iced water bath and poured into a solution of 3.00 g of sodium hydroxide in 250 ml of iced water to precipitate a crystal. The crystal was recovered by filtration and washed with water to obtain 2.92 g of 2-hexyl-5-(6-acetoxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 97.9 %).

Workup

  1. temperatureby refluxing for 1 hour
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled on an iced water bath
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-aaaac94b7d574d949f65e95c68e4b2c4
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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