Acetic Acid → Ethyl 3-phenyl-2-(tert.butylaminosulfonyl)prop-2-enoate

HRID 2050767

Reaktionsgleichung

Reaktionsgleichung von HRID 2050767
[C:1]([NH:5][S:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:25]1([CH:24]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 517165Ammonium AcetateHCID 19833529ethyl-2-(N-tert-butylsulfamoyl)acetate

Produkt 1

HCID 57037021Ethyl 3-phenyl-2-(tert.butylaminosulfonyl)prop-2-enoateAusbeute 72 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

11.2 g (0.05 mol) of ethyl 2-(tert.butylaminosulfonyl)acetate (see J. Org. Chem. 43, p. 4535 (1978)) are dissolved in 50 ml of benzaldehyde, 2 g of ammonium acetate and 2 ml of glacial acetic acid are added, and the mixture is stirred for 2 hours at 60° C. under a water pump vacuum (20 mm). The excess aldehyde is subsequently distilled off, and the residue is digested using n-hexane and recrystallized from isopropanol. 11.2 g (72% of theory) of ethyl 3-phenyl-2-(tert.butylaminosulfonyl)prop-2-enoate of melting point 111°-113° C. are obtained.

Aufarbeitung

  1. distillationThe excess aldehyde is subsequently distilled off
  2. customrecrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-50e92ea2e822489f80998c8691832cdf
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05015284

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