Azobisisobutyronitrile → (1-Hexenyl) sulfide

HRID 66213

반응식

HRID 66213 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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4fa41f875ee41b7ab7911baad8608fc
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04130713

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