Water → N-cyclododecyl-cis-3-(acetylthio)acrylamide

HRID 1463556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463556
[C:1]([S:4]/[CH:5]=[CH:6]\[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH:10]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.O>ClCCl>[CH:10]1([NH:22][C:7](=[O:8])/[CH:6]=[CH:5]\[S:4][C:1](=[O:3])[CH3:2])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 2897CyclododecanamineHCID 8471TriethylamineHCID 86746380cis-3-(Acetylthio)propenoyl chloride

Produkt 1

HCID 86746381N-cyclododecyl-cis-3-(acetylthio)acrylamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred, cooled (0° C.) solution of 3.0 g (0.0162 mol) of cis-3-(acetylthio)propenoyl chloride in 30 ml of dichloromethane under nitrogen was added dropwise 2.98 g (0.0163 mol) of cyclododecylamine as a solution in 30 ml of dichloromethane. After 15 min, 2.27 ml (0.0163 mol) of triethylamine was added dropwise. After 12 h the reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were washed with water, brine, and dried over magnesium sulfate. Filtration and removal of solvents gave 4.5 g of a 2:1 mixture of cis and trans isomers as a tan solid. Purification by flash column chromatography (Merck 60® silica gel, ethyl acetate/hexane eluant) gave 0.5 g (10% yield) of N-cyclododecyl-cis-3-(acetylthio)acrylamide as a white powder where NMR is reported in Table 2.

Aufarbeitung

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and removal of solvents
  5. customgave
  6. addition4.5 g of a 2:1 mixture of cis and trans isomers as a tan solid
  7. customPurification by flash column chromatography (Merck 60® silica gel, ethyl acetate/hexane eluant)

Quellen und Nachweise

ORD-Eintrag
ord-cabb79b40cf741a497d9078ef71e8a16
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300672

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