18-Crown-6 → [1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

HRID 851780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851780
CS(O[CH2:6][CH2:7][N:8]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.[Br-:24].[Li+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[Br:24][CH2:6][CH2:7][N:8]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 2855718-Crown-6HCID 82050Lithium BromideHCID 86736835[1-[2-[(Methylsulfonyl)oxy]ethyl]-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

Produkt 1

HCID 86736837[1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3.4 g. of the ethyl ester product from part (b) are dissolved in 100 ml. of acetone. 1.3 g. (50% excess) of lithium bromide and 0.1 g. of 18-Crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane) are added and the mixture is stirred for three hours at 50°. After the reaction has been completed as determined by TLC, the solvent is distilled off and the reaction mixture is taken up in 50 ml. of methylene chloride and shaken with 50 ml. of water. The organic phase is dried and concentrated to yield the crude product as an oil which, after scratching, crystallizes in several hours. Recrystallization from isopropanol yields purified [1-(2-bromoethyl)-2-(phenylmethylene)hydrazino]-oxoacetic acid, ethyl ester; m.p. 56°-57°.

Aufarbeitung

  1. distillationthe solvent is distilled off
  2. stirringof methylene chloride and shaken with 50 ml
  3. customThe organic phase is dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c096b4d3def441c0a9ffc1de43054507
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386199

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