Azobisisobutyronitrile → (1-Hexenyl) sulfide

HRID 66213

Reaktionsgleichung

Reaktionsgleichung von HRID 66213
Cl.C(O[C:5](=O)[CH:6]([CH2:8][SH:9])N)C.[CH:11]#[C:12][CH2:13][CH2:14][CH2:15][CH3:16].N(C(C)(C)C#N)=N[C:19](C)([CH3:22])[C:20]#N>O1CCOCC1>[CH:11]([S:9][CH:8]=[CH:6][CH2:5][CH2:20][CH2:19][CH3:22])=[CH:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 127321-HexyneHCID 6432754Ethyl 2-amino-3-mercaptopropanoate hydrochloride

Produkt 1

HCID 129639434(1-Hexenyl) sulfide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 12.80 g (68.93 mmol) of DL-cysteine ethyl ester hydrochloride, 25.60 g (311.62 mmol) of 1-hexyne, and 50 mg of 2,2'-azobis-(2-methylpropionitrile) in 250 ml of absolute dioxane was stirred at 60°-65°. under inert gas atmosphere for 20 minutes. After cooling, most of the solvent was evaporated in vacuo. The residue was treated with 150 ml of 1N sodium carbonate solution and extracted three times with ethyl acetate. The organic phases were combined, washed with 3 × 50 ml of saturated brine, dried over anhydrous sodium sulfate and evaporated in vacuo to give 15.90 g (99%) of crude (ethyl 2-aminopropanoate-3-yl) (1-hexenyl) sulfide as a thick pale yellow oil which can be used without further purification in the next step. NMR spectroscopical studies showed that the product is approximately a 1:1 mixture of geometrical isomers.

Aufarbeitung

  1. temperatureAfter cooling, most of the solvent
  2. customwas evaporated in vacuo
  3. additionThe residue was treated with 150 ml of 1N sodium carbonate solution
  4. extractionextracted three times with ethyl acetate
  5. washwashed with 3 × 50 ml of saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d4fa41f875ee41b7ab7911baad8608fc
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04130713

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