Dicyclohexylcarbodiimide → N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704429

Reaktionsgleichung

Reaktionsgleichung von HRID 704429
C1(N=C=NC2CCCCC2)CCCCC1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]2[NH:26][CH:25]([C:27]([OH:29])=O)[CH2:24][S:23]2)[CH:17]=1.ON1C2C=CC=CC=2N=N1.[CH2:40]([NH2:59])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>O1CCCC1.C(OCC)(=O)C>[CH2:40]([NH:59][C:27]([CH:25]1[CH2:24][S:23][CH:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[NH:26]1)=[O:29])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1064161-AminononadecaneHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Produkt 1

HCID 14881554N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamideAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 500 mg of dicyclohexylcarbodiimide in 3 ml of tetrahydrofuran was added dropwise to a mixture of 510 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 490 mg of 1-hydroxybenzotriazole, 680 mg of nonadecylamine and 12 ml of tetrahydrofuran with ice cooling, and the resulting mixture was stirred with ice cooling for 1 hour and then at room temperature for 12 hours. The reaction mixture was diluted with 30 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) and recrystallized from ethyl acetate to give 250 mg of N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamide. Melting point 108°-110° C.

Aufarbeitung

  1. waitat room temperature for 12 hours
  2. filtrationthe insoluble matter was filtered off
  3. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b33b29cc6a4b49c7b2dfc0cdad0ca94c
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04987132

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