Heptanoic Acid → 2-Hexyl-5-(6-heptanoyloxynaphthalene-2-yl)-1,3,4-thiadiazole

HRID 1534768Notes

Reaction equation

HRID 1534768 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1.[CH2:36]([C:42]1[S:43][C:44]([C:47]2[CH:56]=[CH:55][C:54]3[C:49](=[CH:50][CH:51]=[C:52](O)[CH:53]=3)[CH:48]=2)=[N:45][N:46]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>ClCCl>[CH2:36]([C:42]1[S:43][C:44]([C:47]2[CH:56]=[CH:55][C:54]3[C:49](=[CH:50][CH:51]=[C:52]([O:8][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:53]=3)[CH:48]=2)=[N:45][N:46]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 1360772002-Hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole

Product 1

HCID 199079282-Hexyl-5-(6-heptanoyloxynaphthalene-2-yl)-1,3,4-thiadiazoleYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 30 ml-round-bottomed flask, 0.60 g (1.92 mM) of 2-hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole, 0.25 g (1.92 mM) of heptanoic acid were dissolved in 10 ml of dichloromethane. Under stirring, 0.39 g (1.89 mM) of N,N'-dicyclohexylcarbodiimide and 0.02 g of 4-pyrrolidinopyridine were successively added the above solution at room temperature, followed by stirring for 8 hours at room temperature. After the reaction, precipitated N,N'-dicyclohexylurea was filtered off and the filtrate was dried off under reduced pressure to obtain a solid. The solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1) and recrystallized from a mixture solvent (ethanol-ethyl acetate) to obtain 0.42 g of 2-hexyl-5-(6-heptanoyloxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 81.5 %). ##STR139##

Workup

  1. stirringby stirring for 8 hours at room temperature
  2. customAfter the reaction
  3. customprecipitated N,N'-dicyclohexylurea
  4. filtrationwas filtered off
  5. customthe filtrate was dried off under reduced pressure
  6. customto obtain a solid
  7. customThe solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1)
  8. customrecrystallized from a mixture solvent (ethanol-ethyl acetate)

Sources & evidence

ORD record
ord-33406f5327e9400d860c979c99a09d01
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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