Azobisisobutyronitrile → (1-Hexenyl) sulfide

HRID 1156972

반응식

HRID 1156972 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 129639434(1-Hexenyl) sulfide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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 1 N 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.

후처리

  1. temperatureAfter cooling, most of the solvent
  2. customwas evaporated in vacuo
  3. additionThe residue was treated with 150 ml of 1 N 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

출처 및 근거

ORD 기록
ord-787f87e079634238abebc5b121d9fe5f
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04337345

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