Dichloromethane → N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamide

HRID 487132

Reaktionsgleichung

Reaktionsgleichung von HRID 487132
C([C:5]1[CH:6]=[C:7]([CH:13]=[C:14](C(C)(C)C)[C:15]=1O)[CH:8]=[CH:9][C:10]([OH:12])=O)(C)(C)C.[CH2:21]([O:23][C:24]([CH2:26][S:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])[CH3:22].Cl.C(N=C=NCCCN(C)C)C.ClCCl>O>[CH2:21]([O:23][C:24]([CH2:26][S:27][CH2:28][CH2:29][N:30]([CH2:31][CH2:32][CH2:33][CH3:34])[C:10](=[O:12])[CH:9]=[CH:8][C:7]1[CH:6]=[CH:5][CH:15]=[CH:14][CH:13]=1)=[O:25])[CH3:22]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86747655N-ethoxycarbonylmethylthioethyl-n-butylamine

Produkt 1

HCID 67822768N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamideAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

First, 5.53 g of 3,5-di-t-butyl-4-hydroxycinnamic acid, 4.4 g of N-ethoxycarbonylmethylthioethyl-n-butylamine, and 4.0 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) were added to 100 ml of dichloromethane and the mixture was agitated for 3 hours at room temperature. Then, this reaction mixture was poured into water, and after chloroform extraction the chloroform layer was dehydrated with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue so obtained was separated and purified by column chromatography on silica gel with chloroform, after which hexane was added and crystallization yielded 7.34 g of an N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamide derivative (yield 79.5%) in the form of white crystals.

Aufarbeitung

  1. extractionafter chloroform extraction the chloroform layer
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue so obtained
  4. customwas separated
  5. custompurified by column chromatography on silica gel with chloroform
  6. additionafter which hexane was added
  7. customcrystallization

Quellen und Nachweise

ORD-Eintrag
ord-3df5ffdb2f384133825dfbbffd830fcf
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294624

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