1-Hydroxybenzotriazole → HCID 86642922, Verbindung

HRID 1506135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506135
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.Cl.[CH3:12][NH:13][O:14][CH3:15].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl.O>[OH:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])[CH2:6][CH2:7]1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 1511384-Hydroxycyclohexanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 86642922HCID 86642922, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Hydroxycyclohexanecarboxylic acid (10.0 g, 69.4 mmol) and N,O-dimethylhydroxylamine hydrochloride (8.80 g, 90.2 mmol) in dichloromethane (500 mL) was stirred with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (17.3 g, 90.2 mmol), 1-hydroxybenzotriazole (12.2 g, 90.2 mmol) and N,N-diisopropylethylamine (24.2 mL, 139 mmol) at room temperature for one day. After addition of water, the reaction mixture was extracted with chloroform, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)→ethyl acetate) to give the title compound as a yellow oil (9.07 g, yield 70%).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d6bcdfffcf6741b695ffbeacd2d15571
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216999B2

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