Water → [1-[2-[(Methylsulfonyl)oxy]ethyl]-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

HRID 851779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851779
[OH:1][CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>C(Cl)Cl>[CH3:27][S:28]([O:1][CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:30])=[O:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86736836[1-(2-Hydroxyethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

Produkt 1

HCID 86736835[1-[2-[(Methylsulfonyl)oxy]ethyl]-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

26.4 g. of the ethyl ester product from part (a) and 10 g. of triethylamine are dissolved in 200 ml. of methylene chloride. 11.4 g. of methylsulfonyl chloride dissolved in a small amount of methylene chloride are added dropwise at -20°. After two hours, 300 ml. of water are added to the reaction solution and this mixture is stirred for 10 minutes. The organic phase is dried (Na2SO4) and, after distilling off the solvent, a colorless oil is obtained which crystallizes upon scratching. Recrystallization from ethanol yields as a white powder [1-[2-[(methylsulfonyl)oxy]ethyl]-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester; m.p. 93°-95°.

Aufarbeitung

  1. additionare added dropwise at -20°
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. distillationafter distilling off the solvent
  4. customa colorless oil is obtained which
  5. customcrystallizes
  6. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6bd3eba03f1d4727b7a8d8393b98fab8
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386199

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