Hydrazine hydrate (1:1) → 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide

HRID 971310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971310
C[O:2][C:3](=O)[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.O.[NH2:27][NH2:28]>CO>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:5]([CH2:4][C:3]([NH:27][NH2:28])=[O:2])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)(=[O:15])=[O:14])=[CH:17][CH:18]=1)[CH3:24]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 1108126Methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate

Produkt 1

HCID 102700744-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The crude carboxylic acid methyl ester, e.g. methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate (3.816 g, 10.5 mmol), was dissolved in MeOH (30 mL). Hydrazine hydrate was added (3.3 mL). The reaction mixture was stirred overnight at room temperature. A white precipitate was formed. It was isolated by filtration and rinsed with cold MeOH. From mother liquors some more compound could be recovered, affording the desired product, e.g. 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide (2.745 g, 72%) as a colorless solid in 99.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Aufarbeitung

  1. customA white precipitate was formed
  2. customIt was isolated by filtration
  3. washrinsed with cold MeOH
  4. customFrom mother liquors some more compound could be recovered

Quellen und Nachweise

ORD-Eintrag
ord-d94437a0a07249d8b7b56d3c40a37088
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312358B2

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