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Dicyclohexylcarbodiimide → N-(3,4,5-trimethoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704428
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 704428
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[NH2:20].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH3:27][O:26][C:22]1[CH:21]=[C:19]([NH:20][C:12]([CH:10]2[CH2:9][S:8][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:11]2)=[O:14])[CH:18]=[C:17]([O:16][CH3:15])[C:23]=1[O:24][CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 322853,4,5-TrimethoxyanilineHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Produkt 1

HCID 14881598N-(3,4,5-trimethoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamideAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 630 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 520 mg of 3,4,5-trimethoxyaniline, 650 mg of dicyclohexylcarbodiimide and 430 mg of 1-hydroxybenzotriazole in 8 ml of N,N-dimethylformamide was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with aqueous sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (eluent: ethyl acetate) gave 370 mg of N-(3,4,5-trimethoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide. This compound was dissolved in 10 ml of ethyl acetate, and 2 ml of 2N hydrogen chloride solution in dioxane was added. The resultant solid was collected by filtration, washed with ethyl acetate and dried to give mg of N-(3,4,5-trimethoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide dihydrochloride. Melting point 130°-132° C.

Aufarbeitung

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with aqueous sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by silica gel column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fb09ffdbb1b343418f9ab5cda69671af
Quelldatensatz
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04987132

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