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

HRID 1449138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449138
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-466452f8402449648ab2e784f0f00b82
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04189482

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