Hexanoic Acid → 2-(4-Hexylphenyl)-5-(4-hexanoyloxyphenyl)thiazole

HRID 234572

Reaktionsgleichung

Reaktionsgleichung von HRID 234572
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:25](O)(=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 4

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 233547624-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

Produkt 1

HCID 233547882-(4-Hexylphenyl)-5-(4-hexanoyloxyphenyl)thiazoleAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 200 ml-round-bottomed flask, 2.00 g (5.93 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)thiazole, 0.76 g (6.54 mM) of hexanoic acid and 40 ml of dichloromethane were placed and mixed. To the solution, 1.24 g (6.01 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-pyrrolidinopyridine were successively added under stirring at room temperature, followed by further stirring for 7 hours at room temperature to precipitate N,N'-dicyclohexylurea. The resultant N,N'-dicyclohexylurea was filtered off and the solvent of the filtrate was distilled-off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent of toluene-methanol to obtain 1.81 g of 2-(4-hexylphenyl)-5-(4-hexanoyloxyphenyl)thiazole (Yield: 70.1%). ##STR198##

Aufarbeitung

  1. additionmixed
  2. stirringby further stirring for 7 hours at room temperature
  3. customto precipitate N,N'-dicyclohexylurea
  4. filtrationThe resultant N,N'-dicyclohexylurea was filtered off
  5. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  6. customrecrystallized from a mixture solvent of toluene-methanol

Quellen und Nachweise

ORD-Eintrag
ord-6ae0a5b6cb574530aaa67cc74c1ee629
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05595685

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