Benzene → 1-(Allylthiocarbonyl)-trans-decahydroquinoline

HRID 267172Notes

Reaction equation

HRID 267172 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1e1bb83c90544c9396dab4bea109b162
Source dataset
uspto-grants-1976_03
Patent number
US03941579

Reaction notes

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