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p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-[2-ethoxyethylthio(thiocarbonyl)thio]acetate

HRID 1982147
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1982147
[C:1](=[S:9])([S-:8])[S:2][CH2:3][CH2:4][O:5][CH2:6][CH3:7].[K+].[CH2:11]([S:13][CH:14]1[N:17]([CH:18](Cl)[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C:16](=[O:33])[CH2:15]1)[CH3:12]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH2:11]([S:13][CH:14]1[N:17]([CH:18]([S:9][C:1]([S:2][CH2:3][CH2:4][O:5][CH2:6][CH3:7])=[S:8])[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C:16](=[O:33])[CH2:15]1)[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetateHCID 23707565Potassium 2-ethoxyethyl trithiocarbonate

Produkt 1

HCID 13686092p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-[2-ethoxyethylthio(thiocarbonyl)thio]acetateAusbeute 30,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysator
HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A solution of 3.58 g potassium 2-ethoxyethyl trithiocarbonate and 3.7 g benzyltriethylammonium chloride in 100 ml methylene chloride was cooled to 0° C. under a nitrogen atmosphere and a solution of 5.3 g of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate in 50 ml methylene chloride was added dropwise. The reaction mixture was stirred for 1 hour, then washed with three 50 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. (8.6 g). The crude product was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to yield 2.3 g of the title compound as an oil. The IR spectrum of a chloroform solution of the title compound had an absorption at 5.65 micron; and the NMR spectrum in deuterochloroform showed peeks at 1.2(m,6H);2.34-3.77(c,10H);4.7,4.98(m,1H); 5.26(s,2H); 6.62,6.86(s,1H); 7.43(m,2H); and 8.16(m,2H). ppm.

Aufarbeitung

  1. washwashed with three 50 ml portions of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo to an oil
  4. customThe crude product was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e9859f4cf6b64d0caad8386a8522df1b
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04595539

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