Dicyclohexylcarbodiimide → 3-Elaidoyl-1,3-thiazolidine-2-thione

HRID 1883519

Reaktionsgleichung

Reaktionsgleichung von HRID 1883519
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[S:21]1[CH2:25][CH2:24][NH:23][C:22]1=[S:26].C1CCC(N=C=NC2CCCCC2)CC1.C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>CN(C1C=CN=CC=1)C.C1CCC(N=C=NC2CCCCC2)CC1>[C:1]([N:23]1[CH2:24][CH2:25][S:21][C:22]1=[S:26])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 637517Elaidic AcidHCID 27236992-ThiazolidinethioneHCID 18005505Chloroform tetrachloromethane

Produkt 1

HCID 235066693-Elaidoyl-1,3-thiazolidine-2-thioneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10868DicyclohexylcarbodiimideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of elaidic acid (2.0 g, 7.1 mmol), DMAP (86 mg, 0.7 mmol), 1,3-thiazolidine-2-thione (1.0 g, 8.4 mmol) and DCC (1.7 g, 8.2 mmol) in dichloromnethane (20 ml) was stirred under N2 at 0° C. for 1 hour and then at ambient temperature for another 5 hours. Additional DCC (41 mg, 0.2 mmol) was added, andthe reaction was stirred at the same temperature for 2 hours. Work up followed by flash chromatography (SiO2; carbon tetrachloride-chloroform 1:0, 1:1, 0:1) gave 2.56 g (94%) of the title compound as a yellow waxy solid.

Aufarbeitung

  1. waitat ambient temperature for another 5 hours
  2. stirringandthe reaction was stirred at the same temperature for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-da85de3b852a4764aa5b2795694d2fc4
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762175B2

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