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Dimethylamine → HCID 73855551, Verbindung

HRID 2214634
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2214634
[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:11][CH2:12][C:13](O)=[O:14])=[O:9])[C:4](=[O:24])[O:3]1.C(Cl)(=O)C(Cl)=O.[CH3:32][NH:33][CH3:34].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.CN(C)C=O>[CH3:32][N:33]([CH3:34])[C:13]([CH2:12][O:11][N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:24])[O:3][C:2]([CH3:25])([CH3:1])[O:6]1)=[O:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 74058487HCID 74058487, Verbindung

Produkt 1

HCID 73855551HCID 73855551, VerbindungAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of [[2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetyl]-(4-fluorobenzyl)-aminooxy]-acetic acid (0.681 g, 1.93 mmol) in dichloromethane (20 ml) was treated at 22° C. with oxalyl chloride (0.34 ml, 3.9 mmol) and a trace of N,N-dimethylformamide and the resulting mixture was stirred for 1 h. The solvent and excess reagent were then evaporated in vacuo. The residual material was dissolved in dry dichloromethane (10 ml) and added dropwise to a cold (0° C.) solution of dimethylamine (0.18 g, 4.0 mmol) and pyridine (0.25 ml, 3.2 mmol) in dichloromethane. After 2 h, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo and crystallisation of the residue from a mixture of ethyl acetate and hexane gave 0.370 g (50% yield) of the title material as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.77 (6H, s, CH3), 2.91 (3H, s, CH3), 2.97 (3H, s, CH3), 4.53 (2H, s, CH2), 4.93 (2H, s, CH2), 6.43 (1H, s, CH), 7.03 (2H, m, aromatics), 7.41 (2H, m, aromatics).

Aufarbeitung

  1. customThe solvent and excess reagent were then evaporated in vacuo
  2. dissolutionThe residual material was dissolved in dry dichloromethane (10 ml)
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customin vacuo and crystallisation of the residue
  7. additionfrom a mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-58efcf7f43024d839591f6781223f674
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109186B2

Notizen zur Reaktion

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