Benzene → 1-(Allylthiocarbonyl)-trans-decahydroquinoline

HRID 267172노트

반응식

HRID 267172 반응식
[NH:1]1[C@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C(OC(Cl)=[S:18])C=C.[CH:20]1[CH:25]=CC=[CH:22][CH:21]=1>O>[CH2:20]([C:25]([N:1]1[C@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1)=[S:18])[CH:21]=[CH2:22]

참가 물질

6

반응물 4

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 6994352(4aS,8aR)-DecahydroquinolineHCID 15467004Chlorothioformic acid allyl ester

생성물 1

HCID 867330901-(Allylthiocarbonyl)-trans-decahydroquinoline수율 70%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Beneath a solution of 20 g of trans-decahydroquinoline in 100 ml of benzene is introduced a layer consisting of a solution of 5.8 g of sodium hydroxide in 100 ml of water. While stiring vigorously and cooling to 5°-10°C, 20 g of chlorothioformic acid allyl ester are then added dropwise to the mixture. Upon completion of the reaction, stirring is continued for 3 hours, the phases are separated, the benzene phase is washed until neutral, dried, and the benzene evaporated in vacuo. The residual oil is distilled in vacuo to yield 24 g (70% of theory) of 1-(allylthiocarbonyl)-trans-decahydroquinoline (b.p. 110°-116°C/0.2 Torr).

후처리

  1. temperaturecooling to 5°-10°C
  2. customUpon completion of the reaction
  3. customthe phases are separated
  4. washthe benzene phase is washed until neutral,
  5. customdried
  6. customthe benzene evaporated in vacuo
  7. distillationThe residual oil is distilled in vacuo

출처 및 근거

ORD 기록
ord-1e1bb83c90544c9396dab4bea109b162
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03941579

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